Asymmetric Induction in Acyclic Radical Reactions: Enantioselective Syntheses of α-Amino Acids via Carbon-Carbon Bond Forming Radical Reactions.

Article abstract of DOI:10.1016/0040-4020(95)00134-T

The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 1 reacted with allyltri-n-butylstannanes via the corresponding radical 2 by the S_H2' 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.