• Citer

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

par Merschaert, Alain;Delbeke, Pieter;Daloze, Désiré ;Dive, Georges
Référence Tetrahedron letters, 45, 24, page (4697-4701)
Publication Publié, 2004-06

Article révisé par les pairs

• Accès en ligne
• Détails
• Contenu
• Statistiques

Résumé :

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 α,β-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. © 2004 Elsevier Ltd. All rights reserved.