A two-step synthesis of α-keto vinyl carbinols from ketones

Laurent Debien; Samir Z. Zard

doi:10.1021/ol4029594

A two-step synthesis of α-keto vinyl carbinols from ketones

Laurent Debien
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

Conjugate addition of lithium enolates onto terminal alkynyl- and allenyl-sulfoxides furnishes the corresponding allylic sulfoxides. The latter readily undergo a Mislow-Braverman-Evans rearrangement to yield the targeted α-keto vinyl carbinols. This two-step procedure does not require purification of the intermediates and constitutes the shortest approach to α-keto vinyl carbinols.

Original language	English
Pages (from-to)	6066-6069
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	23
DOIs	https://doi.org/10.1021/ol4029594
Publication status	Published - 6 Dec 2013
Externally published	Yes

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10.1021/ol4029594

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title = "A two-step synthesis of α-keto vinyl carbinols from ketones",

abstract = "Conjugate addition of lithium enolates onto terminal alkynyl- and allenyl-sulfoxides furnishes the corresponding allylic sulfoxides. The latter readily undergo a Mislow-Braverman-Evans rearrangement to yield the targeted α-keto vinyl carbinols. This two-step procedure does not require purification of the intermediates and constitutes the shortest approach to α-keto vinyl carbinols.",

author = "Laurent Debien and Zard, \{Samir Z.\}",

year = "2013",

month = dec,

day = "6",

doi = "10.1021/ol4029594",

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journal = "Organic Letters",

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T1 - A two-step synthesis of α-keto vinyl carbinols from ketones

AU - Debien, Laurent

AU - Zard, Samir Z.

PY - 2013/12/6

Y1 - 2013/12/6

N2 - Conjugate addition of lithium enolates onto terminal alkynyl- and allenyl-sulfoxides furnishes the corresponding allylic sulfoxides. The latter readily undergo a Mislow-Braverman-Evans rearrangement to yield the targeted α-keto vinyl carbinols. This two-step procedure does not require purification of the intermediates and constitutes the shortest approach to α-keto vinyl carbinols.

AB - Conjugate addition of lithium enolates onto terminal alkynyl- and allenyl-sulfoxides furnishes the corresponding allylic sulfoxides. The latter readily undergo a Mislow-Braverman-Evans rearrangement to yield the targeted α-keto vinyl carbinols. This two-step procedure does not require purification of the intermediates and constitutes the shortest approach to α-keto vinyl carbinols.

UR - https://www.scopus.com/pages/publications/84890027416

U2 - 10.1021/ol4029594

DO - 10.1021/ol4029594

M3 - Article

AN - SCOPUS:84890027416

SN - 1523-7060

VL - 15

SP - 6066

EP - 6069

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

A two-step synthesis of α-keto vinyl carbinols from ketones

Abstract

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