Todd:Catalytic, Asymmetric Pictet-Spengler Reaction - Revision history

Alice E Williamson: added info on acyliminium reactivity

2013-02-20T13:42:12Z

added info on acyliminium reactivity

←Older revision		Revision as of 13:42, 20 February 2013
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	==Thiourea Organocatalysts==		==Thiourea Organocatalysts==

-	In 2004, Jacobsen reported his initial work on asymmetric catalysis of the acyl-Pictet-Spengler reaction using chiral thioureas. Jacobsen realised the inherent challenge of developing an asymmetric Pictet-Spengler catalyst involved low reactivity of the imine substrate. Additionally, previously reported racemic efforts had involved Lewis acid catalysts paired with highly reactive agents at high temperatures. Jacobsen enhanced the reaction by increasing the electrophilicity of the iminium intermediate through formation of the corresponding N-acyliminium ion ''~~(MAT~~ - ~~Why? We need~~ to ~~explore this concept a bit~~.~~..)~~'' Early screening experiments showed cyclization occuring at -30 °C in 59% ee. While screening individual reaction parameters, Jacobsen discovered that product chirality exhibited a strong dependence upon the structure of the acylating agent, reaction solvent, and temperature.	+	In 2004, Jacobsen reported his initial work on asymmetric catalysis of the acyl-Pictet-Spengler reaction using chiral thioureas. Jacobsen realised the inherent challenge of developing an asymmetric Pictet-Spengler catalyst involved low reactivity of the imine substrate. Additionally, previously reported racemic efforts had involved Lewis acid catalysts paired with highly reactive agents at high temperatures. Jacobsen enhanced the reaction by increasing the electrophilicity of the iminium intermediate through formation of the corresponding N-acyliminium ion. A number of studies on the reactivity of iminium ions have revealed that their substitution pattern accounts for their 'cationic character'. ''N''-acyliminium ions represent some of the most reactive electrophilic systems. The electron-withdrawing group reduces the amount of electron density on the nitrogen and therefore its ability to stabilise the cation. Electrophilic addition to acyliminiums is generally fast and irreversible whereas additions to less reactive ''N''-alkyliminiums can be reversible. Ref
		+
		+	Early screening experiments showed cyclization occuring at -30 °C in 59% ee. While screening individual reaction parameters, Jacobsen discovered that product chirality exhibited a strong dependence upon the structure of the acylating agent, reaction solvent, and temperature.

	[[Image:2004 Jacobsen JACS.png \|thumb\|center\|500px\| '''Scheme: (Jacobsen 2004).''' Catalytic Asymmetric Acyl-Pictet-Spengler Reactions]]		[[Image:2004 Jacobsen JACS.png \|thumb\|center\|500px\| '''Scheme: (Jacobsen 2004).''' Catalytic Asymmetric Acyl-Pictet-Spengler Reactions]]

Alice E Williamson: /* References */

2013-02-08T22:24:45Z

References

←Older revision		Revision as of 22:24, 8 February 2013
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	* Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Brønsted Acid and Palladium Catalysis, M. J. Wanner, E. Claveau, J. H. van Maarseveen and H. Hiemstra, ''Chem. Eur. J.'' '''2011''', ''17'', 13680-13683. [http://dx.doi.org/10.1002/chem.201103150 Paper]		* Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Brønsted Acid and Palladium Catalysis, M. J. Wanner, E. Claveau, J. H. van Maarseveen and H. Hiemstra, ''Chem. Eur. J.'' '''2011''', ''17'', 13680-13683. [http://dx.doi.org/10.1002/chem.201103150 Paper]
	* Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones, J. J. Badillo, A. Silva-Garcia, B. H. Shupe, J. C. Fettinger and A. K. Franz, ''Tetrahedron Lett.'' '''2011''', ''52'', 5550-5553. [http://dx.doi.org/10.1016/j.tetlet.2011.08.071 Paper]		* Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones, J. J. Badillo, A. Silva-Garcia, B. H. Shupe, J. C. Fettinger and A. K. Franz, ''Tetrahedron Lett.'' '''2011''', ''52'', 5550-5553. [http://dx.doi.org/10.1016/j.tetlet.2011.08.071 Paper]
-	*Catalytic Asymmetric Pictet–Spengler- Type Reaction for the Synthesis of Optically Active Indolo[3,4-'''cd'''][1]benzazepines, D-J. Cheng, H-B Wu, S-K. Tian, ''Org. Lett.'' '''2011''', ''13'', 5636-5639.	+	*Catalytic Asymmetric Pictet–Spengler- Type Reaction for the Synthesis of Optically Active Indolo[3,4-'''cd'''][1]benzazepines, D-J. Cheng, H-B Wu, S-K. Tian, ''Org. Lett.'' '''2011''', ''13'', 5636-5639. [http://pubs.acs.org/doi/abs/10.1021/ol202361t?mi=tyek4g&af=R&pageSize=20&searchText=CATALYSIS Paper]
		+

	Organocatalysis Section:		Organocatalysis Section:

Alice E Williamson: /* References */

2013-02-08T22:22:38Z

References

←Older revision		Revision as of 22:22, 8 February 2013
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	* Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Brønsted Acid and Palladium Catalysis, M. J. Wanner, E. Claveau, J. H. van Maarseveen and H. Hiemstra, ''Chem. Eur. J.'' '''2011''', ''17'', 13680-13683. [http://dx.doi.org/10.1002/chem.201103150 Paper]		* Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Brønsted Acid and Palladium Catalysis, M. J. Wanner, E. Claveau, J. H. van Maarseveen and H. Hiemstra, ''Chem. Eur. J.'' '''2011''', ''17'', 13680-13683. [http://dx.doi.org/10.1002/chem.201103150 Paper]
	* Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones, J. J. Badillo, A. Silva-Garcia, B. H. Shupe, J. C. Fettinger and A. K. Franz, ''Tetrahedron Lett.'' '''2011''', ''52'', 5550-5553. [http://dx.doi.org/10.1016/j.tetlet.2011.08.071 Paper]		* Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones, J. J. Badillo, A. Silva-Garcia, B. H. Shupe, J. C. Fettinger and A. K. Franz, ''Tetrahedron Lett.'' '''2011''', ''52'', 5550-5553. [http://dx.doi.org/10.1016/j.tetlet.2011.08.071 Paper]
		+	*Catalytic Asymmetric Pictet–Spengler- Type Reaction for the Synthesis of Optically Active Indolo[3,4-'''cd'''][1]benzazepines, D-J. Cheng, H-B Wu, S-K. Tian, ''Org. Lett.'' '''2011''', ''13'', 5636-5639.

	Organocatalysis Section:		Organocatalysis Section:

Alice E Williamson: /* Brønsted Acid Organocatalysis */

2013-02-08T20:00:05Z

Brønsted Acid Organocatalysis

←Older revision		Revision as of 20:00, 8 February 2013
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	[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]		[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]

-	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee'').	+	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd''][1]-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee'').

	[[Image:2011_Tian_OrgLett_1.png \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Catalytic Asymmetric formation of 7-membered indolo[3,4-''cd'][1]'-benzapines.]]		[[Image:2011_Tian_OrgLett_1.png \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Catalytic Asymmetric formation of 7-membered indolo[3,4-''cd'][1]'-benzapines.]]

Alice E Williamson: /* Brønsted Acid Organocatalysis */

2013-02-08T19:54:19Z

Brønsted Acid Organocatalysis

←Older revision		Revision as of 19:54, 8 February 2013
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	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee'').		Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee'').

-	[[Image:2011_Tian_OrgLett_1 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Catalytic Asymmetric formation of 7-membered indolo[3,4-''cd'][1]'-benzapines.]]	+	[[Image:2011_Tian_OrgLett_1.png \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Catalytic Asymmetric formation of 7-membered indolo[3,4-''cd'][1]'-benzapines.]]

	Control reactions with N–Methyl indole '''x''' gave the corresponding product in just 3% ''ee''. This result suggested that the indole ''NH'' may play an important role in the transition state determining enantioselectivity. Taken together with the postulated importance of the H2NPMP leaving group, Tian proposed a transition complex where the cyclisation precursor '''x''', catalyst '''x''' and trans-imination byproduct '''x''' are organised through hydrogen bonding, resulting in highly enantioselective cyclisation.		Control reactions with N–Methyl indole '''x''' gave the corresponding product in just 3% ''ee''. This result suggested that the indole ''NH'' may play an important role in the transition state determining enantioselectivity. Taken together with the postulated importance of the H2NPMP leaving group, Tian proposed a transition complex where the cyclisation precursor '''x''', catalyst '''x''' and trans-imination byproduct '''x''' are organised through hydrogen bonding, resulting in highly enantioselective cyclisation.


-	[[Image:2011_Tian_OrgLett_2 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' The importance of hydrogen-bonding for enantioselectivity.]]	+	[[Image:2011_Tian_OrgLett_2.png \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' The importance of hydrogen-bonding for enantioselectivity.]]

	A noteworthy experiment showed the reluctance of 4-(2-aminophenyl)-7-azaindole '''x''' to react with PMP protected imine '''x''' under analogous reaction conditions. Intriguingly, the corresponding aldehyde '''x''' did react and gave the desired product '''x''' in good yield and high ''ee'' (77 and 90% respectively). This result again highlights the importance of hydrogen-bonding in the transition state and could also suggest that changing the nucleophile from imine to aldehyde results in a different mechanistic pathway.		A noteworthy experiment showed the reluctance of 4-(2-aminophenyl)-7-azaindole '''x''' to react with PMP protected imine '''x''' under analogous reaction conditions. Intriguingly, the corresponding aldehyde '''x''' did react and gave the desired product '''x''' in good yield and high ''ee'' (77 and 90% respectively). This result again highlights the importance of hydrogen-bonding in the transition state and could also suggest that changing the nucleophile from imine to aldehyde results in a different mechanistic pathway.

-	[[Image:2011_Tian_OrgLett_1 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Aza-indole substrates.]]	+	[[Image:2011_Tian_OrgLett_1.png \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Aza-indole substrates.]]

	==Thiourea Organocatalysts==		==Thiourea Organocatalysts==

Alice E Williamson: /* Brønsted Acid Organocatalysis */

2013-02-08T19:52:47Z

Brønsted Acid Organocatalysis

←Older revision		Revision as of 19:52, 8 February 2013
Line 107:		Line 107:
	[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]		[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]

-	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee''). Control reactions with N–Methyl indole '''x''' gave the corresponding product in just 3% ''ee''. This result suggested that the indole ''NH'' may play an important role in the transition state determining enantioselectivity. Taken together with the postulated importance of the H2NPMP leaving group, Tian proposed a transition complex where the cyclisation precursor '''x''', catalyst '''x''' and trans-imination byproduct '''x'' are organised through hydrogen bonding, resulting in highly enantioselective cyclisation.	+	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee'').

-	~~A noteworthy experiment showed the reluctance of 4-(2-aminophenyl)-7-azaindole~~ '''x''' ~~to react with PMP protected imine '''x''' under analogous reaction conditions. Intriguingly~~, ~~the corresponding aldehyde~~ '''x'~~'' did react and gave the desired product '''x'' in good yield and high ''ee'' (77 and 90% respectively). This result again highlights the importance of hydrogen~~-~~bonding in the transition state and could also suggest that changing the nucleophile from imine to aldehyde results in a different mechanistic pathway~~.	+	[[Image:2011_Tian_OrgLett_1 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Catalytic Asymmetric formation of 7-membered indolo[3,4-''cd'][1]'-benzapines.]]

		+	Control reactions with N–Methyl indole '''x''' gave the corresponding product in just 3% ''ee''. This result suggested that the indole ''NH'' may play an important role in the transition state determining enantioselectivity. Taken together with the postulated importance of the H2NPMP leaving group, Tian proposed a transition complex where the cyclisation precursor '''x''', catalyst '''x''' and trans-imination byproduct '''x''' are organised through hydrogen bonding, resulting in highly enantioselective cyclisation.

-	[[Image:~~2011_Tian_OrgLett.png~~\|thumb\|center\|500px\| '''Scheme: (Tian 2011). ~~Enantioselective PS~~-~~type formation~~ of 7-~~membered indolo~~-~~benzazepines~~.''']]	+
		+	[[Image:2011_Tian_OrgLett_2 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' The importance of hydrogen-bonding for enantioselectivity.]]
		+
		+	A noteworthy experiment showed the reluctance of 4-(2-aminophenyl)-7-azaindole '''x''' to react with PMP protected imine '''x''' under analogous reaction conditions. Intriguingly, the corresponding aldehyde '''x''' did react and gave the desired product '''x''' in good yield and high ''ee'' (77 and 90% respectively). This result again highlights the importance of hydrogen-bonding in the transition state and could also suggest that changing the nucleophile from imine to aldehyde results in a different mechanistic pathway.
		+
		+	[[Image:2011_Tian_OrgLett_1 \|thumb\|center\|500px\| '''Scheme: (Tian 2011).''' Aza-indole substrates.]]

	==Thiourea Organocatalysts==		==Thiourea Organocatalysts==

Alice E Williamson: /* The Catalytic, Asymmetric Pictet-Spengler Reaction */

2013-02-07T19:07:45Z

The Catalytic, Asymmetric Pictet-Spengler Reaction

←Older revision		Revision as of 19:07, 7 February 2013
Line 7:		Line 7:
	Michael A. Tarselli, Biomedisyn Corp., Woodbridge, CT, United States of America<br>		Michael A. Tarselli, Biomedisyn Corp., Woodbridge, CT, United States of America<br>
	Matthew H. Todd, School of Chemistry, The University of Sydney, NSW 2006, Australia<br>		Matthew H. Todd, School of Chemistry, The University of Sydney, NSW 2006, Australia<br>
		+	Alice E. Williamson, School of Chemistry, The University of Sydney, NSW 2006, Australia<br>

	Additional authors - add alphabetically if you contribute something substantial (e.g., the summary of a paper with a scheme). Please include some public place you can be contacted, e.g. a G+ account.<br>		Additional authors - add alphabetically if you contribute something substantial (e.g., the summary of a paper with a scheme). Please include some public place you can be contacted, e.g. a G+ account.<br>

Alice E Williamson: incomplete entry

2013-02-07T19:06:56Z

incomplete entry

←Older revision		Revision as of 19:06, 7 February 2013
Line 106:		Line 106:
	[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]		[[Image:2011_Franz_spirocyclization.png \|thumb\|center\|500px\| '''Scheme: (Franz 2011).''' spirocyclization mechanism - MHT marks this for deletion because the mech is kind of obvious from what has been already discussed.]]

-	~~('''KAB - Working on Tian 2011 OrgLett''')~~	+	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo[3,4-''cd'][1]'-benzapines '''x'''. Tian and co-workers reported the phosphoric acid catalysed reaction of 4-(2-aminoaryl)insoles '''x''' with ''para''-methoxybenezene (PMB) protected aryl imines. X (Scheme X). The researchers screened a number of imine and aldehyde nucleophiles and found that: 1) PMB to be the optimum imine protecting group, 2) the reaction proceeded with higher ''ee'' at greater concentration and 3) PMB protected imines reacted with higher enantioselectivity than their corresponding aldehyde (90 compared to 83% ''ee''). Control reactions with N–Methyl indole '''x''' gave the corresponding product in just 3% ''ee''. This result suggested that the indole ''NH'' may play an important role in the transition state determining enantioselectivity. Taken together with the postulated importance of the H2NPMP leaving group, Tian proposed a transition complex where the cyclisation precursor '''x''', catalyst '''x''' and trans-imination byproduct '''x'' are organised through hydrogen bonding, resulting in highly enantioselective cyclisation.
-	Chiral phosphoric acids have also been used in catalytic asymmetric PS-type reactions to give 7-membered indolo-benzapines. Tian and co-workers reported the X (Scheme X). A number of imine~~/aldehydes were screened. An increase in ee was obtained when~~ the ~~N-paramethoxy~~ imine, ~~X, relative~~ to ~~p-chlorobenzaldehyde to produce~~ the ~~same~~ product~~, X~~. ~~The indolo NH was crucial for enantioselectivity. Tian~~ suggested the NH ~~was involved~~ in ~~hydrogen bonding~~ with the H2NPMP leaving group ~~which was supposed to be further involved in H~~-bonding with the ~~BINAP~~-~~derived phosphoric acid~~.	+
		+	A noteworthy experiment showed the reluctance of 4-(2-aminophenyl)-7-azaindole '''x''' to react with PMP protected imine '''x''' under analogous reaction conditions. Intriguingly, the corresponding aldehyde '''x''' did react and gave the desired product '''x'' in good yield and high ''ee'' (77 and 90% respectively). This result again highlights the importance of hydrogen-bonding in the transition state and could also suggest that changing the nucleophile from imine to aldehyde results in a different mechanistic pathway.
		+
		+
	[[Image:2011_Tian_OrgLett.png\|thumb\|center\|500px\| '''Scheme: (Tian 2011). Enantioselective PS-type formation of 7-membered indolo-benzazepines.''']]		[[Image:2011_Tian_OrgLett.png\|thumb\|center\|500px\| '''Scheme: (Tian 2011). Enantioselective PS-type formation of 7-membered indolo-benzazepines.''']]

Alice E Williamson: /* Papers we're not including, and why (arranged by date) */

2013-02-05T11:28:39Z

Papers we're not including, and why (arranged by date)

←Older revision		Revision as of 11:28, 5 February 2013
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	* An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (-)-Talcarpine and (-)-Anhydromacrosalhine-methine, X. Liao, H. Zhou, J. Yu and J. M. Cook, ''J. Org. Chem.'' '''2006''', ''71'', 8884-8890. [http://dx.doi.org/10.1021/jo061652u Paper] - presumed diastereoselective, but relevant chemistry is actually in J. Org. Chem. 2000, 65, 3173.		* An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (-)-Talcarpine and (-)-Anhydromacrosalhine-methine, X. Liao, H. Zhou, J. Yu and J. M. Cook, ''J. Org. Chem.'' '''2006''', ''71'', 8884-8890. [http://dx.doi.org/10.1021/jo061652u Paper] - presumed diastereoselective, but relevant chemistry is actually in J. Org. Chem. 2000, 65, 3173.
	* Application of modified Pictet–Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines, S. Duggineni, D. Sawant, B. Saha, B. Kundu, ''Tetrahedron'' '''2006''', ''62'', 3228–3241. - extension to picket-spengler but not catalytic asymmetric.		* Application of modified Pictet–Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines, S. Duggineni, D. Sawant, B. Saha, B. Kundu, ''Tetrahedron'' '''2006''', ''62'', 3228–3241. - extension to picket-spengler but not catalytic asymmetric.
-	* Cascade Reactions in Total Synthesis, K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, ''Angew. Chem. Int. Ed'' '''2006''', ''45'', 7134–7186. - features pictet-spengler but not catalytic asymmetric.	+	* Cascade Reactions in Total Synthesis, K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, ''Angew. Chem. Int. Ed.'' '''2006''', ''45'', 7134–7186. [http://onlinelibrary.wiley.com/doi/10.1002/anie.200601872/abstract Paper] - features pictet-spengler but not catalytic asymmetric.
	* Synthesis of (±)-Strychnofoline via a Highly Convergent Selective Annulation Reaction, A. Lerchner, E. M. Carreira ''Chem. Eur. J.'' '''2006''', ''12'', 8208–8219. [http://onlinelibrary.wiley.com/doi/10.1002/chem.200600957/abstract] - not catalytic or pictet-spengler		* Synthesis of (±)-Strychnofoline via a Highly Convergent Selective Annulation Reaction, A. Lerchner, E. M. Carreira ''Chem. Eur. J.'' '''2006''', ''12'', 8208–8219. [http://onlinelibrary.wiley.com/doi/10.1002/chem.200600957/abstract] - not catalytic or pictet-spengler
	* Total Synthesis of the Opioid Agonistic Indole Alkaloid Mitragynine and the First Total Syntheses of 9-Methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol, J. Ma, W. Yin, H. Zhou and J. M. Cook, ''Org. Lett.'' '''2007''', ''9'', 3491-3494. [http://dx.doi.org/10.1021/ol071220l Paper] - diastereoselective.		* Total Synthesis of the Opioid Agonistic Indole Alkaloid Mitragynine and the First Total Syntheses of 9-Methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol, J. Ma, W. Yin, H. Zhou and J. M. Cook, ''Org. Lett.'' '''2007''', ''9'', 3491-3494. [http://dx.doi.org/10.1021/ol071220l Paper] - diastereoselective.

Alice E Williamson: /* Papers we're not including, and why (arranged by date) */

2013-02-05T11:27:00Z

Papers we're not including, and why (arranged by date)

←Older revision		Revision as of 11:27, 5 February 2013
Line 325:		Line 325:
	* An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (-)-Talcarpine and (-)-Anhydromacrosalhine-methine, X. Liao, H. Zhou, J. Yu and J. M. Cook, ''J. Org. Chem.'' '''2006''', ''71'', 8884-8890. [http://dx.doi.org/10.1021/jo061652u Paper] - presumed diastereoselective, but relevant chemistry is actually in J. Org. Chem. 2000, 65, 3173.		* An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (-)-Talcarpine and (-)-Anhydromacrosalhine-methine, X. Liao, H. Zhou, J. Yu and J. M. Cook, ''J. Org. Chem.'' '''2006''', ''71'', 8884-8890. [http://dx.doi.org/10.1021/jo061652u Paper] - presumed diastereoselective, but relevant chemistry is actually in J. Org. Chem. 2000, 65, 3173.
	* Application of modified Pictet–Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines, S. Duggineni, D. Sawant, B. Saha, B. Kundu, ''Tetrahedron'' '''2006''', ''62'', 3228–3241. - extension to picket-spengler but not catalytic asymmetric.		* Application of modified Pictet–Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines, S. Duggineni, D. Sawant, B. Saha, B. Kundu, ''Tetrahedron'' '''2006''', ''62'', 3228–3241. - extension to picket-spengler but not catalytic asymmetric.
		+	* Cascade Reactions in Total Synthesis, K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, ''Angew. Chem. Int. Ed'' '''2006''', ''45'', 7134–7186. - features pictet-spengler but not catalytic asymmetric.
	* Synthesis of (±)-Strychnofoline via a Highly Convergent Selective Annulation Reaction, A. Lerchner, E. M. Carreira ''Chem. Eur. J.'' '''2006''', ''12'', 8208–8219. [http://onlinelibrary.wiley.com/doi/10.1002/chem.200600957/abstract] - not catalytic or pictet-spengler		* Synthesis of (±)-Strychnofoline via a Highly Convergent Selective Annulation Reaction, A. Lerchner, E. M. Carreira ''Chem. Eur. J.'' '''2006''', ''12'', 8208–8219. [http://onlinelibrary.wiley.com/doi/10.1002/chem.200600957/abstract] - not catalytic or pictet-spengler
	* Total Synthesis of the Opioid Agonistic Indole Alkaloid Mitragynine and the First Total Syntheses of 9-Methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol, J. Ma, W. Yin, H. Zhou and J. M. Cook, ''Org. Lett.'' '''2007''', ''9'', 3491-3494. [http://dx.doi.org/10.1021/ol071220l Paper] - diastereoselective.		* Total Synthesis of the Opioid Agonistic Indole Alkaloid Mitragynine and the First Total Syntheses of 9-Methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol, J. Ma, W. Yin, H. Zhou and J. M. Cook, ''Org. Lett.'' '''2007''', ''9'', 3491-3494. [http://dx.doi.org/10.1021/ol071220l Paper] - diastereoselective.