Talk:Todd:Catalytic, Asymmetric Pictet-Spengler Reaction

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Revision as of 20:59, 20 January 2012 by Matthew Todd (talk | contribs) (→‎Introduction/Background to the PS Reaction: added early examples references)
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Use this page for discussion. Preface questions/comments with initials. Reply to questions but don't delete the question. If things are resolved, move them to the "resolved" section at the bottom of the page.

General Comments

MHT - Jan19 - the page is quite long. We could consider splitting into sections if anyone is having a browser problem, but otherwise we keep as-is. Much more convenient having everything on one page.

Papers that are relevant and need to be included for the first time

These papers are relevant and have not yet been included. They need a summary paragraph and possibly a scheme

None currently

Papers that have not yet been included, but have been referenced by others

These papers need to be checked for relevance. They typically have come from other, relevant papers, but the relevance may not be clear. If they are relevant and need including, move the citation from this section to the "needs to be included" section on this page. If you wish to then actually include it in the review, write "your initials - doing" next to the paper

Introduction/Background to the PS Reaction

These general reviews need to be checked, to ensure we have not missed anything, and as inspiration for thoughts on the reaction mechanism.

Early examples: probably rac/achiral

  • Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030-2036.
  • Tatsui, G. J. Pharm. Soc. Jpn. 1928, 48, 92 (may be 453-459).
  • Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797- 1842 (especially their tryptophan ester strategy)
  • Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341-3370.
  • Nature: Naoi, M.; Maruyama, W.; Nagy, G. M. Neurotoxicology 2004, 25, 193- 204

Check for the importance of the structural motifs constructed with the reaction:

  • Brown, R. T. In Indoles; Saxton, J. E., Ed.; Wiley- Interscience: New York, 1983; Part 4 (The Monoterpenoid Indole Alkaloids)
  • Bentley, K. W. Nat. Prod. Rep. 2004, 21, 395-424 and references therein
  • W. Jiang, J. Guan, M. J. Macielag, S. Zhang, Y. Qiu, P. Kraft, S.

Also possibly: Bhattacharjee, T. M. John, D. Haynes-Johnson, S. Lundeen, Z. Sui, J. Med. Chem. 2005, 48, 2126 – 2133

Specifically with respect to carbolines:

  • Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761–793
  • Yu, J.; Wang, T.; Liu, X.; Deschamps, J.; Anderson, J. F.; Liao, X.; Cook, J. M. J. Org. Chem. 2003, 68, 7565–7581
  • Liao, X.; Zhou, H.; Yu, J.; Cook, J. M. J. Org. Chem. 2006, 71, 8884–8890
  • Ma, J.; Yin, W.; Zhou, H.; Cook, J. M. Org. Lett. 2007, 9, 3491–3494
  • Herraiz, T. J. Chromatogr. A 2000, 881, 483–499
  • Herraiz, T.; Galisteo, J.; Chamorro, C. J. Agric. Food Chem. 2003, 51, 2168–2173.

Diastereoelective Reactions

Diastereoselective (note: must be catalytic for full inclusion - may be no examples):

  • Czarnocki, Z.; MacLean, D. B.; Szarek, W. A. Can. J. Chem. 1986, 64, 2205-2210.
  • Czarnocki, Z.; Suh, D.; MacLean, D. B.; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1992, 70, 1555-1561.
  • Czarnocki, Z.; Mieckzkowsi, J. B.; Kiegiel, J.; Arazn ́y, Z. Tetrahyedron: Asymmetry 1995, 6, 2899-2902.
  • Tsuji, R.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2003, 14, 177- 180.

Lewis Acids

  • Hino, T.; Nakagawa, M. Heterocycles 1998, 49, 499-531.
  • Leighton Angew 2009

Bronsted Acid Section

Akiyama (2004) says these earlier reports "claim" the use of chiral B acids - is that the case, and is the work relevant here?

  • C. Palomo, M. Oiarbide, J. M. Garcia, A. Gonzalez, A. Lecumberri, A. Linden, J. Am. Chem. Soc. 2002, 124, 10288
  • N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094
  • Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.

Akiyama (2004) also mentions these "metal salt" versions:

  • J. Inanaga, Y. Sugimoto, T. Hanamoto, New J. Chem. 1995, 19, 707
  • H. Furuno, T. Hanamoto, Y. Sugimoto, J. Inanaga, Org. Lett. 2000, 2, 49

Previous Bronsted acid example from Terada

  • Schreiner, P. R. Chem. Soc. ReV. 2003, 32, 289.
  • Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
  • McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003,125, 12094.

Example of chiral charged Brønsted acid catalyst:

  • Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004,126, 3418.

Jacobsen Strecker and Mannich history, from Terada

  • Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
  • Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
  • Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
  • Su, J. T.; Vachal, P.; Jacobsen, E. N. AdV. Synth. Catal. 2001, 343, 197.
  • Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10013.
  • Wenzel, A. G.; Lalonde, M. P.; Jacobsen, E. N. Synlett 2003, 1919.
  • Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.

See also:

  • Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
  • Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto,Y. Org. Lett. 2004, 6, 625.

Copper complex example from Terada:

  • Marigo, M.; Kjærsgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem.- Eur. J. 2003, 9, 2359.

The strengths of these chiral phosphoric acids is governed by: Akiyama Chem Rev 2007 Terada ChemComm 2008

Reviews to check through for comments on mechanism of reactions and possible applications of Bronsted acids that have not yet been applied to the PS.

  • S.J. Connon, Angew. Chem. Int. Ed. 2006, 45, 3909–3912
  • T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999 – 1010
  • M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520–1543
  • Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407–3417
  • Terada Synthesis 2010, 1929-1982
  • List, Top. Curr. Chem. 2010, 291, 395-456
  • Rueping Angewandte 2011, 50, 6706-6720

Organocatalysis Section

Jacobsen 2007 JACS, 129, 13404

Smaller items to do

KAB - Jan21 - The scheme for 2009 Hiemstra with the H8-BINOL phosphoric acid in the box, doesn't have the H8-BINOL phosphoric acid in the box. Still has the BINOL.

Resolved

-- 1. KAB attempt to understand 2000 Koomen OrgLett

The figure for Table 1 gives diasteromeric ratios. Where are the diastereomers? I only the possibility for enantiomers in the product. Where's the other stereogenic centre?

They also mentioned "hydrolysis of the starting material" numerous times. I'm assuming they mean hydrolysis of the N-S bond (there doesn't seem any other reasonable place for hydrolysis of the SM to occur), but I just wanted to check. This comment resolved since this paper no longer included in the review. --

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