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

Andrei V. Malkov, Monica Orsini, Daniele Pernazza, Ken W. Muir, Vratislav Langer, Premji Meghani and Pavel Kocovsky*

*Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK, Email: p.kocovskychem.gla.ac.uk

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/ol025654m (free Supporting Information)


Abstract

A heterobidenate bipyridine monoxide (PINDOX) catalyzes the Sakurai-Hosomi-type allylation of aromatic and heteroaromatic aldehydes with high enantioselectivities. The sterochemical outcome is mainly controlled by the axial chirality in PINDOX.

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proposed transition state



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

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


Key Words

Hosomi-Sakurai Reaction, Allylation, Organocatalysis


ID: J54-Y2002-730