Communication

Highly Diastereoselective Construction of Fused Carbocycles from Cyclopropane-1,1-dicarboxylates and Cyclic Enol Silyl Ethers: Scope, Mechanism, and Origin of Diastereoselectivity

  1. Dr. Jian-Ping Qu1,
  2. Dr. Yong Liang2,
  3. Hao Xu1,
  4. Dr. Xiu-Li Sun1,
  5. Prof. Dr. Zhi-Xiang Yu2,*,
  6. Prof. Dr. Yong Tang1,*

Article first published online: 20 JAN 2012

DOI: 10.1002/chem.201103495

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 8, pages 2196–2201, February 20, 2012

Additional Information

How to Cite

Qu, J.-P., Liang, Y., Xu, H., Sun, X.-L., Yu, Z.-X. and Tang, Y. (2012), Highly Diastereoselective Construction of Fused Carbocycles from Cyclopropane-1,1-dicarboxylates and Cyclic Enol Silyl Ethers: Scope, Mechanism, and Origin of Diastereoselectivity. Chem. Eur. J., 18: 2196–2201. doi: 10.1002/chem.201103495

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) 21-5492-5078

  2. 2

    Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (P.R. China)

*Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (P.R. China)

Publication History

  1. Issue published online: 10 FEB 2012
  2. Article first published online: 20 JAN 2012
  3. Manuscript Revised: 16 DEC 2011
  4. Manuscript Received: 7 NOV 2011

Funded by

  • Natural Sciences Foundation of China. Grant Numbers: 20821002, 20932008, 20825205
  • Major State Basic Research Development Program. Grant Number: 2009CB825300
  • Chinese Academy of Sciences

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (1193K)

Keywords:

  • cycloaddition;
  • cyclopropane;
  • density functional calculations;
  • diastereoselectivity;
  • reaction mechanisms
Thumbnail image of graphical abstract

Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through CuII/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme).

View Full Article with Supporting Information (HTML) Get PDF (1193K)