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Design of a new class of chiral C2-symmetric dipyridylmethane ligands and their application in asymmetric catalysis

✍ Scribed by Giorgio Chelucci; Giovanni Loriga; Gabriele Murineddu; Gerard A. Pinna

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 204 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02066-x

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✦ Synopsis

A new class of chiral C 2 -symmetric dipyridylmethane ligands was prepared from naturally occurring monoterpenes, according to a method based on a double Michael-azaannellation-aromatization sequence. These ligands were assessed in the enantioselective palladium-catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate and in the copper-catalyzed cyclopropanation of styrene with ethyl diazoacetate. Enantioselectivity up to 88% ee was obtained.

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