A general asymmetric synthesis of syn- and anti-β-Substituted cysteine and serine derivatives

Chiyi Xiong, Wei Wang, Victor J Hruby

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Abstract

A stereodivergent synthetic route has been developed to make the optically pure anti- and syn-β-substituted cysteine and serine derivatives. In this approach, the key intermediates, > 94% enantiomerically pure cyclic sulfates 3 and aziridines 7, were prepared from α,β-unsaturated esters 1, employing the Sharpless asymmetric dihydroxylation. The high regio- and stereoselective ring-opening reactions of cyclic sulfates and aziridines provided enantiomerically pure β-substituted cysteine and serine derivatives.

Original languageEnglish (US)
Pages (from-to)3514-3517
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number10
DOIs
Publication statusPublished - May 17 2002

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ASJC Scopus subject areas

  • Organic Chemistry

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