Talk:Todd:Catalytic, Asymmetric Pictet-Spengler Reaction

Use this page for discussion. Preface questions/comments with initials.

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.

Things that need doing (updated 20/01/12):

Papers to Summarise/Check for Suitability Enantioselective/Lewis Acids:

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

Enantioselective/Bronsted Acids: The strengths of these chiral phosphoric acids is governed by: Akiyama Chem Rev 2007 Terada ChemComm 2008 Reviews: a) S.J. Connon, Angew. Chem. Int. Ed. 2006, 45, 3909–3912 b) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999 – 1010 c) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520–1543 d) Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407–3417 e) Terada Synthesis 2010, 1929-1982 f) List, Top. Curr. Chem. 2010, 291, 395-456 g) Rueping Angewandte 2011, 50, 6706-6720

Archived/inactive discussions:

1. KAB attempt to understand 2000 Koomen OrgLett (archived since this paper no longer included)

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.