Cu(II)-catalyzed acylation by thiol esters under neutral conditions: Tandem acylation-wittig reaction leading to a one-pot synthesis of butenolides

Kazumasa Matsuo; Mitsuru Shindo

doi:10.1021/ol102407k

Cu(II)-catalyzed acylation by thiol esters under neutral conditions: Tandem acylation-wittig reaction leading to a one-pot synthesis of butenolides

Kazumasa Matsuo, Mitsuru Shindo

Department of Fundamental Organic Chemistry

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

71 Citations (Scopus)

Abstract

The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

Original language	English
Pages (from-to)	5346-5349
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	22
DOIs	https://doi.org/10.1021/ol102407k
Publication status	Published - Nov 19 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102407k

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abstract = "The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.",

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PY - 2010/11/19

Y1 - 2010/11/19

N2 - The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

AB - The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

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Cu(II)-catalyzed acylation by thiol esters under neutral conditions: Tandem acylation-wittig reaction leading to a one-pot synthesis of butenolides

Abstract

All Science Journal Classification (ASJC) codes

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