Prev. Article Table of Contents

Letter

Chiral 2,2‘-Bipyridine-Type N-Monoxides as Organocatalysts in the Enantioselective Allylation of Aldehydes with Allyltrichlorosilane^†

Supporting Info

Andrei V. Malkov,*^‡ Monica Orsini,^‡ Daniele Pernazza,^‡ Ken W. Muir,^‡ Vratislav Langer,^§ Premji Meghani, and Pavel Ko

ovský*^‡

Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K., Department of Inorganic Environmental Chemistry, Chalmers University of Technology, 41296 Gteborg, Sweden, and AstraZeneca R&D, Loughborough, Leics. LE11 5RH, U.K.

Org. Lett., 2002, 4 (6), pp 1047–1049

DOI: 10.1021/ol025654m

Publication Date (Web): February 16, 2002

†

Dedicated to Professor John E. McMurry on the occasion of his 60th birthday.

Email address for A.V.M.: amalkov@chem.gla.ac.uk.

‡

University of Glasgow.

Chalmers University of Technology.

AstraZeneca.

, p.kocovsky@chem.gla.ac.uk

Abstract

The Sakurai−Hosomi-type allylation of aromatic and heteroaromatic aldehydes can be catalyzed by the new heterobidenate bipyridine monoxide PINDOX with high enantioselectivities. The sterochemical outcome is mainly controlled by the axial chirality in PINDOX, which in turn is determined by the annulated terpene units.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue March 21, 2002
Received February 1, 2002

Recommend & Share

Related Content

METHOX: A New Pyridine N-Oxide Organocatalyst for the Asymmetric Allylation of Aldehydes with AllyltrichlorosilanesOrganic Letters
- 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
  Organic Letters 2005 7 (15), pp 3219–3222
  Abstract: 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 ...
  Abstract | Full Text HTML | Hi-Res PDF
Asymmetric Allylation of Aldehydes with Chiral Lewis BasesThe Journal of Organic Chemistry
- Asymmetric Allylation of Aldehydes with Chiral Lewis Bases
  Scott E. Denmark, Diane M. Coe, Norman E. Pratt, Brian D. Griedel
  The Journal of Organic Chemistry 1994 59 (21), pp 6161–6163
  Abstract | Hi-Res PDF
(S)-3,3‘-Dimethyl-2,2‘-biquinoline N,N‘-Dioxide as an Efficient Catalyst for Enantioselective Addition of Allyltrichlorosilanes to AldehydesJournal of the American Chemical Society
- (S)-3,3‘-Dimethyl-2,2‘-biquinoline N,N‘-Dioxide as an Efficient Catalyst for Enantioselective Addition of Allyltrichlorosilanes to Aldehydes
  Makoto Nakajima, Makoto Saito, Motoo Shiro, and Shun-ichi Hashimoto
  Journal of the American Chemical Society 1998 120 (25), pp 6419–6420
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Chiral 2,2‘-Bipyridine-Type N-Monoxides as Organocatalysts in the Enantioselective Allylation of Aldehydes with Allyltrichlorosilane^†