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Issue 16, 2002
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Asymmetric synthesis of β-pyridyl-β-amino acid derivatives

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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-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee.

Graphical abstract: Asymmetric synthesis of β-pyridyl-β-amino acid derivatives

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Supplementary files

Article information


Submitted
14 May 2002
Accepted
02 Jul 2002
First published
18 Jul 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1858-1868
Article type
Paper

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

S. D. Bull, S. G. Davies, David. J. Fox, M. Gianotti, P. M. Kelly, C. Pierres, E. D. Savory and A. D. Smith, J. Chem. Soc., Perkin Trans. 1, 2002, 1858
DOI: 10.1039/B204653A

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