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The Asymmetric Synthesis of α-Amino Acids via the Addition of Grignard Reagents to Imine Derivatives. by David P.G. Hamon; Ralph A. Massy-Westropp; Pasquale Razzino is a Chemistry article available to read on EtoBox.

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Ablracr: The eater 8-phenyhnenthyl N-Boc-glycinate Sa, 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 I-phenylmenthyl (S)-N-Boc-2-alkylglycinates with high diitereoseltxtivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid. As well as the twenty common u-amino acids, there exist hundreds of other non-proteinogenic amino acids'. Many of these are biologically active and the unique biological action usually resides in one enantiomer. Although the twenty common amino acids can be readily obtained from natural soumes2. this is not necessarily true for the rarer analogues and in many cases asymmetric synthesis may well be the best method to obtain quantities of them Even though a large number of ways to prepare such compounds existss, the importance of enantiomerically pure amino acids and the diverse range of structures found, means there is still a need to develop new ways to prepare such compounds in optically active form. The asymmetric synthesis of a-amino acids described in

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Author

David P.G. Hamon; Ralph A. Massy-Westropp; Pasquale Razzino

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1992

Language

EN

Field

Chemistry (Physical Sciences)