METHOX:  A New Pyridine N-Oxide Organocatalyst for the Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes†

Andrei V. Malkov,* Mark Bell,‡ Fabiomassimo Castelluzzo, and Pavel Koovský*;
Department of Chemistry, Joseph Black Building, WestChem, University of Glasgow, Glasgow G12 8QQ, Scotland, UK
Org. Lett., 2005, 7 (15), pp 3219–3222
DOI: 10.1021/ol050972h
Publication Date (Web): June 28, 2005
Copyright © 2005 American Chemical Society
†

 Dedicated to Dr. Jiří Závada on the occasion of his 70th birthday.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Current address:  Kemisk Institut, Aarhus Universitet, 8000 Aarhus C, Denmark.

, amalkov@chem.gla.ac.uk, ; , pavelk@chem.gla.ac.uk

Abstract

Abstract Image

Allylation of aromatic aldehydes with allyltrichlorosilane is catalyzed by the new terpene-derived pyridine N-oxide (+)-METHOX (≤5 mol %) in MeCN with high enantioselectivities (≤96% ee) and conversion rates; this catalyst retains high selectivity even at room temperature.

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History

  • Published In Issue July 21, 2005
  • Received April 29, 2005

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