Reference : The rational design of modified cinchona alkaloid catalysts. Application to a new asymme...

	Document type :	Scientific journals : Article
	Discipline(s) :	Physical, chemical, mathematical & earth Sciences : Chemistry
	To cite this reference:	http://hdl.handle.net/2268/30019

Title :	The rational design of modified cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes
Language :	English
Author, co-author :	Merschaert, Alain [> > > >]
	Delbeke, Pieter [> > > >]
	Daloze, Désiré [> > > >]
	Dive, Georges [Université de Liège - ULg > > Centre d'ingénierie des protéines >]
Publication date :	7-Jun-2004
Journal title :	Tetrahedron Letters
Publisher :	Pergamon-Elsevier Science Ltd
Volume :	45
Issue/season :	24
Pages :	4697-4701
Audience :	International
ISSN :	0040-4039
City :	Oxford
Keywords :	[en] alkaloids ; oxa-Michael ; asymmetric ; catalysis
Abstract :	[en] A new asymmetric synthesis of 2-substituted chiral chromanes has been achieved. The key step is the intramolecular conjugate addition of a phenolic nucleophile on a alpha,beta-unsaturated ester catalyzed by Cinchona alkaloids. The high ee's obtained with cinchonine and its derivatives have been rationalized by ab initio quantum chemistry calculations of transition state structures. (C) 2004 Elsevier Ltd. All rights reserved.
Target :	Researchers ; Professionals
Permalink :	http://hdl.handle.net/2268/30019

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