Chirality transferring [3,3] sigmatropic rearrangement of (1-acyloxy-2-alkenyl)trialkylsilane synthesis of optically active vinylsilane-containing alpha-amino acid

A vinylsilane-containing alpha -amino acid and alpha,alpha -disubstituted a lpha -amino acid 2 having two contiguous asymmetric carbon centers at their alpha and beta positions were synthesized in an optically active form by e ster-enolate Claisen rearrangement of the alpha -acyloxysilane 1 as the key step, where the chirality of an alpha -acyloxy-TBDMS group was completely transferred to the rearranged product. Chirality 13,357-365, 2001. (C) 2001 Wiley-Liss, Inc.