Chirality Transferring [3,3] Sigmatropic Rearrangement of (1-Acyloxy-2-alkenyl)trialkylsilane Synthesis of Optically Active Vinylsilane-Containing α-Amino Acid

摘要

A vinylsilane-containing α-amino acid and α,α-disubstituted α-amino acid 2 having two contiguous asymmetric carbon centers at their α and β positions were synthesized in an optically active form by ester-enolate Claisen rearrangement of the α-acyloxysilane 1 as the key step, where the chirality of an α-acyloxy-TBDMS group was completely transferred to the rearranged product.