Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether

Xiongwei Shi; Francis X. Webster; James Kallmerten; Jerrold Meinwald

doi:10.1016/0040-4039(95)01500-H

Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether

Xiongwei Shi, Francis X. Webster, James Kallmerten, Jerrold Meinwald

Department of Chemistry

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Abstract

The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.

Original language	English (US)
Pages (from-to)	7197-7200
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	40
DOIs	https://doi.org/10.1016/0040-4039(95)01500-H
State	Published - Oct 2 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether",

abstract = "The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.",

author = "Xiongwei Shi and Webster, {Francis X.} and James Kallmerten and Jerrold Meinwald",

note = "Funding Information: by the NSF (Grant DCB8608007) and the NIH (AI12020) is gratefully acknowledged.",

year = "1995",

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doi = "10.1016/0040-4039(95)01500-H",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether

AU - Shi, Xiongwei

AU - Webster, Francis X.

AU - Kallmerten, James

AU - Meinwald, Jerrold

N1 - Funding Information: by the NSF (Grant DCB8608007) and the NIH (AI12020) is gratefully acknowledged.

PY - 1995/10/2

Y1 - 1995/10/2

N2 - The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.

AB - The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.

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U2 - 10.1016/0040-4039(95)01500-H

DO - 10.1016/0040-4039(95)01500-H

M3 - Article

AN - SCOPUS:0029164288

SN - 0040-4039

VL - 36

SP - 7197

EP - 7200

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether

Abstract

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