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

2002; American Chemical Society; Volume: 4; Issue: 6 Linguagem: Inglês

10.1021/ol025654m

1523-7060

Andrei V. Malkov, Monica Orsini, Daniele Pernazza, K.W. Muir, Vratislav Langer, Premji Meghani, Pavel Kočovský,

Chemical Synthesis and Reactions

[reaction: see text] 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.