The rational design of modified cinchona alkaloid catalysts. Application to a new asymmetric synthesis of chiral chromanes

Merschaert, Alain; Delbeke, Pieter; Daloze, Désiré; Dive, Georges

doi:10.1016/j.tetlet.2004.04.090

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.

2004 • In Tetrahedron Letters, 45 (24), p. 4697-4701

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https://hdl.handle.net/2268/30019

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10.1016/j.tetlet.2004.04.090

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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 :

Issue :

Pages :

4697-4701

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 28 November 2009

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Bibliography

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