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

Chelucci, Giorgio Adolfo and Loriga, Giovanni and Murineddu, Gabriele and Pinna, Gérard Aimé (2002) Design of a new class of chiral C2-symmetric dipyridylmethane ligands and their application in asymmetric catalysis. Tetrahedron Letters, Vol. 43 (47), p. 8599-8602. ISSN 0040-4039. Article.

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DOI: 10.1016/S0040-4039(02)02066-X

Abstract

A new class of chiral C2-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.

Item Type:Article
ID Code:388
Status:Published
Refereed:Yes
Uncontrolled Keywords:Dipyridylmethane ligands, allylic alkylation, cyclopropanation, enantioselectivity
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Pergamon / Elsevier
ISSN:0040-4039
Copyright Holders:© 2002 Elsevier
Deposited On:18 Aug 2009 10:02

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