Enolate claisen rearrangement of glycolate esters

James Kallmerten; Thomas J. Gould

doi:10.1016/S0040-4039(00)88390-2

Enolate claisen rearrangement of glycolate esters

James Kallmerten, Thomas J. Gould

Department of Chemistry

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

59 Scopus citations

Abstract

The enolate Claisen rearrangement of O-protected allylic glycolates yields functionalized acylic systems with high syn and anti stereoselectivity. This procedure is the key step in a short synthesis of threo-4-methylheptan-3-ol, an aggregation pheromone of the European elm bark beetle.

Original language	English (US)
Pages (from-to)	5177-5180
Number of pages	4
Journal	Tetrahedron Letters
Volume	24
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(00)88390-2
State	Published - 1983

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)88390-2

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title = "Enolate claisen rearrangement of glycolate esters",

abstract = "The enolate Claisen rearrangement of O-protected allylic glycolates yields functionalized acylic systems with high syn and anti stereoselectivity. This procedure is the key step in a short synthesis of threo-4-methylheptan-3-ol, an aggregation pheromone of the European elm bark beetle.",

author = "James Kallmerten and Gould, {Thomas J.}",

year = "1983",

doi = "10.1016/S0040-4039(00)88390-2",

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AU - Kallmerten, James

AU - Gould, Thomas J.

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AB - The enolate Claisen rearrangement of O-protected allylic glycolates yields functionalized acylic systems with high syn and anti stereoselectivity. This procedure is the key step in a short synthesis of threo-4-methylheptan-3-ol, an aggregation pheromone of the European elm bark beetle.

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U2 - 10.1016/S0040-4039(00)88390-2

DO - 10.1016/S0040-4039(00)88390-2

M3 - Article

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SP - 5177

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Enolate claisen rearrangement of glycolate esters

Abstract

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