Communication

Catalytic Enantioselective Hosomi–Sakurai Conjugate Allylation of Cyclic Unsaturated Ketoesters†

  1. Manami Shizuka,
  2. Marc L. Snapper Prof.

Article first published online: 27 MAY 2008

DOI: 10.1002/anie.200800628

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 27, pages 5049–5051, June 23, 2008

Additional Information

How to Cite

Shizuka, M. and Snapper, Marc L. (2008), Catalytic Enantioselective Hosomi–Sakurai Conjugate Allylation of Cyclic Unsaturated Ketoesters. Angew. Chem. Int. Ed., 47: 5049–5051. doi: 10.1002/anie.200800628

Author Information

  1. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-1442 http://www2.bc.edu/∼snapper/

  1. †

    Support from the NIH (GM-57212) is gratefully acknowledged. We thank the Hoveyda group for use of their chiral GLC and HPLC. We also thank Prof. James Morken for helpful discussions.

Publication History

  1. Issue published online: 16 JUN 2008
  2. Article first published online: 27 MAY 2008
  3. Manuscript Revised: 7 MAR 2008
  4. Manuscript Received: 8 FEB 2008

Funded by

  • NIH. Grant Number: GM-57212

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Keywords:

  • allylation;
  • asymmetric synthesis;
  • copper;
  • homogeneous catalysis;
  • Michael reaction
Thumbnail image of graphical abstract

No fancy catalyst required: The copper-catalyzed enantioselective conjugate allylation of activated cyclic enones affords products in up to >98 % ee. Reactions proceed to high conversion in the presence of commercially available Cu(OTf)2 and bis(oxazoline) ligand 1. The allylated products are useful precursors for the synthesis of chiral building blocks.

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