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2010-有机通讯-Cu-酰化.pdf

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2010-有机通讯-Cu-酰化

ORGANIC LETTERS Cu(II)-Catalyzed Acylation by Thiol 2010 Vol. 12, No. 22 Esters Under Neutral Conditions: 5346-5349 Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides Kazumasa Matsuo† and Mitsuru Shindo*,‡ Interdisciplinary Graduate School of Engineering Sciences, Kyushu Uni Versity, and Institute for Materials Chemistry and Engineering, Kyushu UniVersity, Kasuga-koen, Kasuga 816-8580, Japan shindo@cm.kyushu-u.ac.jp Received October 5, 2010 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. Thiol esters are among the most important easily handled, ester in the syntheses of sundiversifolide.3 In this reaction, stable acylating agents of alcohols in organic syntheses and an excess of the Wittig reagent and high temperatures were biological systems.1 Generally, acylations using a thiol ester required to complete the reaction. Since the reaction with are carried out under basic conditions to activate the alcohols. the Wittig reag