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CO2-Activation for γ-Butyrolactones and Its Application in the Total Synthesis of (±)-Heteroplexisolide E

  1. Suhua Li1,
  2. Prof. Dr. Shengming Ma1,2,*

Article first published online: 16 JUL 2012

DOI: 10.1002/asia.201200467

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 10, pages 2411–2418, October 2012

Additional Information

How to Cite

Li, S. and Ma, S. (2012), CO2-Activation for γ-Butyrolactones and Its Application in the Total Synthesis of (±)-Heteroplexisolide E. Chem. Asian J., 7: 2411–2418. doi: 10.1002/asia.201200467

Author Information

  1. 1

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032(P. R. China), Fax: (+86) 21-6260-9305

  2. 2

    Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P. R. China)

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032(P. R. China), Fax: (+86) 21-6260-9305

Publication History

  1. Issue published online: 17 SEP 2012
  2. Article first published online: 16 JUL 2012
  3. Manuscript Received: 26 MAY 2012

Funded by

  • National Basic Research Program of China. Grant Number: 2009CB825300
  • National Natural Science Foundation of China. Grant Number: 20732005
  • Shanghai Municipal Committee of Science. Grant Number: 08dj1400100

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Keywords:

  • alkynes;
  • butyrolactones;
  • carbon dioxide;
  • hydrocarboxylation;
  • nickel

Abstract

An efficient nickel(0)-catalyzed highly regio- and stereoselective hydrocarboxylation of homopropargylic alcohols with ZnEt2 in the presence of CO2 (1 atm, balloon) to synthesize α-alkylidene-γ-butyrolactones is described. The catalyst is highly active and can be applied for the synthesis of (optically active) mono- or bicyclic α-alkylidene-γ-butyrolactones with excellent regio- and stereoselectivity and good functional group tolerance. The potential of the reaction has been demonstrated in the first synthesis of (±)-heteroplexisolide E.

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