Communication

Gold(I)-Catalyzed Asymmetric Cycloisomerization of Eneallenes into Vinylcyclohexenes†

  1. Michael A. Tarselli1,
  2. Anthony R. Chianese Dr.1,
  3. Stephen J. Lee Dr.2,
  4. Michel R. Gagné Prof.1

Article first published online: 27 JUL 2007

DOI: 10.1002/anie.200701959

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 46, Issue 35, pages 6670–6673, September 3, 2007

Additional Information

How to Cite

Tarselli, Michael A., Chianese, Anthony R., Lee, Stephen J. and Gagné, Michel R. (2007), Gold(I)-Catalyzed Asymmetric Cycloisomerization of Eneallenes into Vinylcyclohexenes. Angew. Chem. Int. Ed., 46: 6670–6673. doi: 10.1002/anie.200701959

Author Information

  1. 1

    University of North Carolina—Chapel Hill, Chapel Hill, NC 27599-3290, USA, Fax: (+1) 919-962-6342

  2. 2

    U.S. Army Research Office, P.O. Box 12211, Research Triangle Park, NC 27709, USA

  1. †

    The authors thank Prof. Ross Widenhoefer (Duke) for a sample of [(R)-tBu2MeO-BIPHEP(AuCl)2] and Prof. Wenbin Lin (UNC) for a sample of 4,4′-(TMS)2binap. Postdoctoral funding from the National Research Council (A.R.C.) and from the National Institutes of General Medicine (GM-60578) is also greatly appreciated.

Publication History

  1. Issue published online: 28 AUG 2007
  2. Article first published online: 27 JUL 2007
  3. Manuscript Revised: 31 MAY 2007
  4. Manuscript Received: 3 MAY 2007

Funded by

  • National Research Council
  • National Institutes of General Medicine. Grant Number: GM-60578

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Keywords:

  • asymmetric synthesis;
  • C[BOND]C coupling;
  • gold;
  • homogeneous catalysis
Thumbnail image of graphical abstract

Coming around: Cycloisomerization of eneallenes by cationic gold(I) catalysts produces vinylcyclohexene derivatives in up to 77 % ee, using [3,5-xylyl-binap(AuCl)2] and AgOTf additive (see scheme; 3,5-xylyl-binap=2,2′-bis(di(3,5-xylyl)phosphino)-1,1′-binaphthyl). The procedure is amenable to the synthesis of mono- and bicyclic products and is tolerant of ester, alcohol, and amide groups.

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