Communication

Enantioselective and Catalytic Method for α-Crotylation of Aldehydes with a Kinetic Self-Refinement of Stereochemistry

  1. Andrei V. Malkov Prof. Dr.1,2,
  2. Mikhail A. Kabeshov1,
  3. Maciej Barłog1,
  4. Pavel Kočovský Prof. Dr.1

Article first published online: 2 JAN 2009

DOI: 10.1002/chem.200802224

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 15, Issue 7, pages 1570–1573, February 2, 2009

Additional Information

How to Cite

Malkov, Andrei V., Kabeshov, Mikhail A., Barłog, M. and Kočovský, P. (2009), Enantioselective and Catalytic Method for α-Crotylation of Aldehydes with a Kinetic Self-Refinement of Stereochemistry. Chem. Eur. J., 15: 1570–1573. doi: 10.1002/chem.200802224

Author Information

  1. 1

    Department of Chemistry, WestChem, University of Glasgow, Glasgow G12 8QQ (UK), Fax: (+44) 141-330-4888

  2. 2

    Current Address: Department of Chemistry, Loughborough University, Leicestershire, LE11 3TU (UK), Fax: (+44) 1509-22-3925

Publication History

  1. Issue published online: 26 JAN 2009
  2. Article first published online: 2 JAN 2009
  3. Manuscript Received: 27 OCT 2008

Funded by

  • EPSRC. Grant Numbers: G/T27051/01, EP/E011179/1

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Keywords:

  • allylation;
  • asymmetric catalysis;
  • rearrangement;
  • silanes;
  • stereoselectivity

Abstract

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Kinetic refinery: A practical, highly stereoselective, two-step catalytic protocol for the α-allylation of aldehydes, starting from crotyltrichlorosilanes, has been developed (see scheme). In each reaction step, one of the stereoisomers reacted faster than the other, which resulted in a kinetic stereochemical (E/Z) self-refinement of the system and led to the formation of virtually enantiomerically and geometrically pure linear homoallylic alcohols in high yield.

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