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Binaphthalene-templated N,S- and N,P-heterobidentate ligands with an achiral oxazoline pendant: synthesis and assessment in asymmetric catalysis

Gladiali, Serafino Gabriele and Loriga, Giovanni and Medici, Serenella and Taras, Rossana Maria (2003) Binaphthalene-templated N,S- and N,P-heterobidentate ligands with an achiral oxazoline pendant: synthesis and assessment in asymmetric catalysis. Journal of Molecular Catalysis A. Chemical, Vol. 196 (1-2), p. 27-38. ISSN 1381-1169. Article.

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DOI: 10.1016/S1381-1169(02)00632-5

Abstract

Novel chiral binaphthalene-core ligands where an oxazoline pendant is flanked by a sulfur 6, or by an atropisomeric phosphite donor 5, have been synthesized using the hydroxy binaphthyl oxazoline 7 as the common starting material. This intermediate is obtained in high e.e. by Ni-catalyzed asymmetric heterocoupling of two suitably 1,2-disubstituted naphthalene derivatives. Ligands 5 and 6 feature a stereogenic axis as the unique source of chirality. They display chelate binding towards Rh(I) centres affording cationic complexes which have been inspected for their catalytic activity in several asymmetric reactions with modest success. The Pd catalyst derived from the sulfur-containing oxazoline 6a provides up to 66% e.e. in the allylic alkylation of 1,3-diphenylallyl esters with dimethyl malonate.

Item Type:Article
ID Code:5173
Status:Published
Refereed:Yes
Uncontrolled Keywords:Binaphthyl oxazoline ligands, axial chirality, N,X-heterodonor ligands, Rh(I) complexes, Pd-catalyzed allylic alkylation
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Elsevier Science
ISSN:1381-1169
Copyright Holders:© 2002 Elsevier Science
Deposited On:03 Dec 2010 10:00

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