Synthesis of Optically Active Bifunctional Building Blocks through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

Anthoni W. van Zijl, Fernando López,† Adriaan J. Minnaard, and Ben L. Feringa*
Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands
J. Org. Chem., 2007, 72 (7), pp 2558–2563
DOI: 10.1021/jo0625655
Publication Date (Web): March 8, 2007
Copyright © 2007 American Chemical Society
†

 Current address:  Departamento de Química Orgánica, Universidad de Santiago de Compostela, Avda. de las Ciencias, s/n, 15782, Santiago de Compostela, Spain.

,
*

 To whom correspondence should be addressed. Fax:  +31 50 363 4296. Phone:  +31 50363 4235.

, B.L.Feringa@rug.nl

Abstract

Abstract Image

Enantioselective copper-catalyzed allylic alkylations were performed on allylic bromides with a protected hydroxyl or amine functional group using several Grignard reagents and Taniaphos L1 as a ligand. The terminal olefin moiety in the products was transformed into various functional groups without racemization, providing facile access to a variety of versatile bifunctional chiral building blocks.

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History

  • Published In Issue March 30, 2007
  • Received December 14, 2006

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