Organic Chemistry Portal

Abstracts

Search:

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: shindocm.kyushu-u.ac.jp

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

DOI: 10.1021/ol102407k (free Supporting Information)


Abstract

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.

see article for more examples



Key Words

Butenolides, Oxone, Wittig Reaction


ID: J54-Y2010-3300