A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

Jiro Tsuji; Kiyomi Sakai; Hideo Nagashima; Isao Shimizu

doi:10.1016/0040-4039(81)80167-0

A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

Jiro Tsuji^*, Kiyomi Sakai, Hideo Nagashima, Isao Shimizu

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl₂ in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

Original language	English
Pages (from-to)	131-134
Number of pages	4
Journal	Tetrahedron Letters
Volume	22
Issue number	2
DOIs	https://doi.org/10.1016/0040-4039(81)80167-0
Publication status	Published - 1981

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters",

abstract = "A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.",

author = "Jiro Tsuji and Kiyomi Sakai and Hideo Nagashima and Isao Shimizu",

year = "1981",

doi = "10.1016/0040-4039(81)80167-0",

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pages = "131--134",

journal = "Tetrahedron Letters",

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T1 - A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

AU - Tsuji, Jiro

AU - Sakai, Kiyomi

AU - Nagashima, Hideo

AU - Shimizu, Isao

PY - 1981

Y1 - 1981

N2 - A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

AB - A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

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