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Stereoselective Construction of Spiro(butyrolactonepyrrolidines) by Highly Efficient Copper(I)/TF-BiphamPhos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition

  1. Tang-Lin Liu1,
  2. Zhao-Lin He1,
  3. Hai-Yan Tao1,
  4. Prof. Dr. Chun-Jiang Wang1,2,*

Article first published online: 4 JUN 2012

DOI: 10.1002/chem.201103876

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 26, pages 8042–8046, June 25, 2012

Additional Information

How to Cite

Liu, T.-L., He, Z.-L., Tao, H.-Y. and Wang, C.-J. (2012), Stereoselective Construction of Spiro(butyrolactonepyrrolidines) by Highly Efficient Copper(I)/TF-BiphamPhos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition. Chem. Eur. J., 18: 8042–8046. doi: 10.1002/chem.201103876

Author Information

  1. 1

    College of Chemistry and Molecular Sciences, Wuhan University, 430072 (P.R. China), Fax: (+86) 27-68754067

  2. 2

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Fenglin Road, Shanghai, 230032 (P.R. China)

*College of Chemistry and Molecular Sciences, Wuhan University, 430072 (P.R. China), Fax: (+86) 27-68754067

Publication History

  1. Issue published online: 18 JUN 2012
  2. Article first published online: 4 JUN 2012
  3. Manuscript Received: 10 DEC 2012

Funded by

  • NSFC. Grant Numbers: 20972117, 21172176
  • Ministry of Education. Grant Number: IRT1030
  • 973 program. Grant Number: 2011CB808600
  • SRFDP. Grant Number: 20090141110042

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Keywords:

  • asymmetric catalysis;
  • cycloaddition;
  • diastereoselectivity;
  • enantioselectivity;
  • spiro compounds
Thumbnail image of graphical abstract

Pyrrole into one: The catalytic asymmetric 1,3-dipolar cycloaddition of cyclic aldimino esters has been accomplished for the first time, enabling facile access to spiro(butyrolactonepyrrolidines) containing one spiro quaternary center and three tertiary stereogenic centers (see scheme). The catalytic system performs well with a broad range of substrates, furnishing synthetically useful adducts in high yields, with excellent diastereo- and enantioselectivities under mild conditions.

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