Alpha-Trialkylsilyl amino acids: Preparations and applications

ORGN 88

Guodong Liu and Scott McN. Sieburth. Department of Chemistry, Temple University, 1901 N. 13th Street, Philadelphia, PA 19122
Asymmetric reverse-aza-Brook rearrangement of N-Boc-N-trialkylsilyl allylamine yields an enantiomerically enriched alpha-amino allylsilane. Oxidative cleavage of the alkene leads to a Boc-protected amino acid with the configuration of naturally occurring amino acids (L). Advancements in this methodolgy now makes it possible to readily prepare multi-gram quantities of the amino acid precursor in a single operation from the Boc-protected amine.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004