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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

Kazumasa Matsuo and Mitsuru Shindo*

*Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, and Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga 816-8580, Japan, Email:

K. Matuso, M. Shindo, Org. Lett., 2010, 12, 5346-5349.

DOI: 10.1021/ol102407k


A Cu(II)-catalyzed acylation of acyloins with a thiol ester present in Wittig reagents under neutral conditions through a push-pull mechanism enables a one-pot lactonization to yield butenolides. The synthetic utility of this method for the synthesis of natural products is shown.

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Key Words

Butenolides, Oxone, Wittig Reaction

ID: J54-Y2010-3300