135263-84-2Relevant academic research and scientific papers
Asymmetric Induction in Acyclic Radical Reactions: Enantioselective Syntheses of α-Amino Acids via Carbon-Carbon Bond Forming Radical Reactions.
Hamon, David P. G.,Massy-Westropp, Ralph A.,Razzino, Pasquale
, p. 4183 - 4194 (2007/10/02)
The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 1 reacted with allyltri-n-butylstannanes via the corresponding radical 2 by the SH2' 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.
The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives
Hamon, David P. G.,Massy-Westropp, Ralph A.,Razzino, Pasquale
, p. 5163 - 5178 (2007/10/02)
The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.
Enantioselective Syntheses of α-Amino Acids via Carbon-Carbon Bond Forming Radical Reactions
Hamon, David P. G.,Massy-Westropp, Ralph A.,Razzino, Pasquale
, p. 722 - 724 (2007/10/02)
The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 2 reacts with unsaturated stannanes to give unsaturated amino acid derivatives with high diastereoselectivity.
