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

Andrei V. Malkov, Mark Bell, Fabiomassimo Castelluzzo and Pavel Kocovsky*

*Department of Chemistry, Joseph Black Building, WestChem, University of Glasgow, Glasgow G12 8QQ, Scotland, UK, Email: amalkovchem.gla.ac.uk, p.kocovskychem.gla.ac.uk

A. V. Malkov, M. Bell, F. Castelluzzo, P. Kocovsky, Org. Lett., 2005, 7, 3219-3222.

DOI: 10.1021/ol050972h (free Supporting Information)


Abstract

A new terpene-derived pyridine N-oxide catalyzes the allylation of aromatic aldehydes with allyltrichlorosilane in MeCN with high enantioselectivities and conversion rates. The catalyst retains high selectivity even at room temperature.

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

A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kocovsky, Org. Lett., 2002, 4, 1047-1049.

DOI: 10.1021/ol050972h


Key Words

Hosomi-Sakurai Reaction, Allylation, Organocatalysis


ID: J54-Y2005-3200