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Issue 20, 1999
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Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E )-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups

Abstract

Regio- and stereo-selective ring-opening reactions of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E )-α,β-enoates with acids such as methanesulfonic acid (MSA) or trifluoroacetic acid (TFA) have been found. These ring-opening reactions are useful for the stereoselective synthesis of a couple of diastereomeric (E )-alkene dipeptide isosteres from a single substrate of γ,δ-epimino (E )-α,β-enoate, and for the convenient preparation of δ-aminated γ-hydroxy α,β-enoates.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1999, 2983-2996
Article type
Paper

Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E )-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups

H. Tamamura, M. Yamashita, Y. Nakajima, K. Sakano, A. Otaka, H. Ohno, T. Ibuka and N. Fujii, J. Chem. Soc., Perkin Trans. 1, 1999, 2983
DOI: 10.1039/A904671B

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