Stereospecific reduction of a β-keto-nitrile: Formation of a single indolic β-hydroxy-nitrile from a mixture of tautomers and diastereoisomers

Patrick D. Bailey, Sean P. Hollinshead, Madeleine H. Moore, Keith M. Morgan, David I. Smith, John M. Vernon

Research output: Contribution to journalArticle

Abstract

The ß-keto-nitrile 2, which is an advanced intermediate for the synthesis of several indole alkaloids, is composed of a mixture of enol/keto tautomers, and of diastereoisomers; nevertheless, reduction with sodium borohydride yields essentially a single diastereoisomer 3.

Original languageEnglish
Pages (from-to)3585-3586
Number of pages2
JournalTetrahedron Letters
Volume35
Issue number21
DOIs
Publication statusPublished - 1994

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