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.kocovsky
chem.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
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.
see article for more examples
proposed
transition state
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
