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Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides

  1. Roberto Fernández de la Pradilla Prof. Dr.,
  2. Carlos Montero Dr.,
  3. Mariola Tortosa Dr.,
  4. Alma Viso Dr.

Article first published online: 26 NOV 2008

DOI: 10.1002/chem.200801680

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 15, Issue 3, pages 697–709, January 5, 2009

Additional Information

How to Cite

Fernández de la Pradilla, R., Montero, C., Tortosa, M. and Viso, A. (2009), Asymmetric Claisen Rearrangements on Chiral Vinyl Sulfoxides. Chem. Eur. J., 15: 697–709. doi: 10.1002/chem.200801680

Author Information

  1. Instituto de Química Orgánica General, C.S.I.C. Juan de la Cierva 3, 28006 Madrid (Spain), Fax: (+34) 915-644-853

Publication History

  1. Issue published online: 29 DEC 2008
  2. Article first published online: 26 NOV 2008
  3. Manuscript Received: 13 AUG 2008

Funded by

  • DGI. Grant Number: CTQ2006–04522/BQU
  • CM. Grant Number: S-SAL-0249–2006

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Keywords:

  • diastereoselectivity;
  • rearrangement;
  • sulfides;
  • sulfones;
  • sulfoxides

Abstract

Highly diastereoselective Claisen rearrangements of acyclic allyl vinyl ethers bearing a chiral sulfoxide at C-5 provide γ-δ-unsaturated aldehydes or ketones with up to two consecutive asymmetric centers in the molecule whilst preserving a useful vinyl sulfoxide. The reactivity of related vinyl sulfides and sulfones has also been examined in this work.

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