Article (Scientific journals)
The rational design of modified cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes
Merschaert, Alain; Delbeke, Pieter; Daloze, Désiré et al.
2004In Tetrahedron Letters, 45 (24), p. 4697-4701
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Keywords :
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.
Disciplines :
Chemistry
Author, co-author :
Merschaert, Alain
Delbeke, Pieter
Daloze, Désiré
Dive, Georges ;  Université de Liège - ULiège > Centre d'ingénierie des protéines
Language :
English
Title :
The rational design of modified cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes
Publication date :
07 June 2004
Journal title :
Tetrahedron Letters
ISSN :
0040-4039
Publisher :
Pergamon-Elsevier Science Ltd, Oxford, United Kingdom
Volume :
45
Issue :
24
Pages :
4697-4701
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 28 November 2009

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