Asymmetric synthesis of β-pyridyl-β-amino acid derivatives

…, M Gianotti, PM Kelly, C Pierres, ED Savory…

Index: Bull, Steven D.; Davies, Stephen G.; Fox, David J.; Gianotti, Massimo; Kelly, Peter M.; Pierres, Camille; Savory, Edward D.; Smith, Andrew D. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 16 p. 1858 - 1868

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Citation Number: 28

Abstract

The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4- methoxybenzylamide to tert-butyl 3-(3-pyridyl)-and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)-and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4- ...