A general method for the synthesis of enantiomerically pure β-substituted, β-amino acids through α-substituted succinic acid derivatives

…, JS Johnson, DHB Ripin, JS Tedrow

Index: Evans, David A.; Wu, Leester D.; Wiener, John J. M.; Johnson, Jeffrey S.; Ripin, David H. B.; Tedrow, Jason S. Journal of Organic Chemistry, 1999 ,  vol. 64,  # 17  p. 6411 - 6417

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Citation Number: 133

Abstract

A general procedure for the synthesis of enantiopure β-substituted, β-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R= Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (≥ 93: 7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the ...