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Synthesis and application in asymmetric copper(I)-catalyzed allylic oxidation of a new chiral 1,10-phenanthroline derived from pinene

Chelucci, Giorgio Adolfo and Loriga, Giovanni and Murineddu, Gabriele and Pinna, Gérard Aimé (2002) Synthesis and application in asymmetric copper(I)-catalyzed allylic oxidation of a new chiral 1,10-phenanthroline derived from pinene. Tetrahedron Letters, Vol. 43 (19), p. 3601-3604. ISSN 0040-4039. Article.

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DOI: 10.1016/S0040-4039(02)00549-X

Abstract

A convenient and rapid method for the preparation of chiral C2-symmetric 1,10-phenanthrolines is reported. As an example of this procedure the synthesis of new 1,10-phenanthroline (+)-7 and its 5,6-dihydro derivative (+)-6 from (−)-β-pinene is described. These ligands have been assessed in asymmetric copper(I)-catalyzed allylic oxidation of cycloalkenes affording enantioselectivities up to 71%.

Item Type:Article
ID Code:383
Status:Published
Refereed:Yes
Uncontrolled Keywords:1,10-phenanthrolines, copper complex, allylic oxidation, 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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