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Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane

Chelucci, Giorgio Adolfo and Baldino, Salvatore and Pinna, Gérard Aimé and Benaglia, Maurizio and Buffa, Laura and Guizzetti, Stefania (2008) Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane. Tetrahedron, Vol. 64 (32), p. 7574-7582. ISSN 0040-4020. Article.

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DOI: 10.1016/j.tet.2008.05.105

Abstract

The synthesis of enantiomerically pure C2-symmetric dipyridylmethane ligands and related N,N′-dioxides is reported. A procedure for the synthesis of a few new enantiomerically pure C2-symmetric pyridine N-oxides and the preparation of four pyridine N-oxides with oxygen and nitrogen atoms as further coordinating elements in the heterocycle framework is described. All compounds were prepared from naturally occurring monoterpenes. These new compounds were assessed as organocatalysts in two different reactions, namely the allylation of aldehydes with allyltrichlorosilane that afforded homoallylic alcohols in good yields and up to 85% ee and the stilbene oxide opening by the addition of tetrachlorosilane that gave chlorohydrin in quantitative yield and up to 70% ee.

Item Type:Article
ID Code:1807
Status:Published
Refereed:Yes
Uncontrolled Keywords:Pyridine N-oxides, organocatalysis, monoterpenes, allyltrichlorosilane, epoxide opening
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:0040-4020
Copyright Holders:© 2008 Elsevier
Deposited On:18 Aug 2009 10:06

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