Alpha-amino allyl silanes are readily prepared in high enantiomeric purity by asymmetric reverse-aza-Brook rearrangement of an N-silyl allyl amine 1. The trimethylsilyl-substituted allylsilane can be converted to 2 and cyclized by treatment with fluoride. The diastereoselectivity of this cyclization was found to be solvent dependent. In all cases, however, the cyclized product was racemic. Oxidation of the alkene gave the naturally occurring amino acid 4.
Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster