ChemInform Abstract: Atropisomeric Amides: Stereoselective Enolate Chemistry and Enantioselective Synthesis via a New SmI2-Mediated Reduction.

✍ Scribed by Adam D. Hughes; David A. Price; Nigel S. Simpkins

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199941019

✦ Synopsis

Atropisomeric Amides: Stereoselective Enolate Chemistry and Enantioselective Synthesis via a New SmI 2 -Mediated Reduction.

-The SmI 2 -mediated reduction of α-functionalized amides offers a new method to prepare amides like (II). This reaction proceeds well for different types of tertiary amides and effects the removal of α-bromo, α-acetoxy, and α-benzyloxy functions. It can be applied to prepare optically pure atropisomeric amides like (IIa). The amide products undergo alkylation with high diastereoselectivity. Reductive removal of the auxiliary leads to primary alcohols. -(HUGHES,