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

doi:10.1016/S0040-4039(00)73246-1

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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 language	English
Pages (from-to)	3585-3586
Number of pages	2
Journal	Tetrahedron Letters
Volume	35
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)73246-1
Publication status	Published - 1994

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

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.",

author = "Bailey, {Patrick D.} and Hollinshead, {Sean P.} and Moore, {Madeleine H.} and Morgan, {Keith M.} and Smith, {David I.} and Vernon, {John M.}",

year = "1994",

doi = "10.1016/S0040-4039(00)73246-1",

language = "English",

volume = "35",

pages = "3585--3586",

journal = "Tetrahedron Letters",

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T1 - Stereospecific reduction of a β-keto-nitrile

T2 - Formation of a single indolic β-hydroxy-nitrile from a mixture of tautomers and diastereoisomers

AU - Bailey, Patrick D.

AU - Hollinshead, Sean P.

AU - Moore, Madeleine H.

AU - Morgan, Keith M.

AU - Smith, David I.

AU - Vernon, John M.

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

U2 - 10.1016/S0040-4039(00)73246-1

DO - 10.1016/S0040-4039(00)73246-1

M3 - Article

SN - 0040-4039

VL - 35

SP - 3585

EP - 3586

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

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

Abstract

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