ASYMMETRIC INDUCTION IN ACYCLIC RADICAL REACTIONS - ENANTIOSELECTIVE SYNTHESES OF ALPHA-AMINO-ACIDS VIA CARBON-CARBON BOND-FORMING RADICAL REACTIONS

The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 1 reacted with allyltri-n-butylstannanes via the corresponding radical 2 by the S(H)2' mechanism to give (2S) allyl amino acid derivatives with high diastereoselectivity. The reaction of 1 with triphenyl(1,2-propadienyl)stannane and triphenyl(2-propynyl)stannane gave the (2S) allenyl and (2S) propargyl amino acid derivatives respectively also with high diastereoselectivity but by a different mechanism.