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Modification of the face selectivity in asymmetric induction by cyclodextrins through the formation of three-component inclusion compounds |
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| Authors: | E. Renard A. Deratani F. Djedaini-Pilard B. Perly |
| Affiliation: | (1) Laboratoire de Physico-Chimie des Biopolymères, UMR 27, CNRS-Université Paris Val de Marne, 2 rue H. Dunant, 94320 Thiais, France;(2) Laboratoire des Matériaux et Procédés Membranaires, UMR 9987, CNRS -ENSCM - Universitè Montpellier 11, 2 place E Bataillon, 34095 Montpellier cedex 5, France;(3) Laboratoire de RMN Haute Résolution, DRECAM-SCM, CEA, CE Saclay, 91191 Gif-sur Yvette, France |
| Abstract: | Stoichiometric amounts of triethylamine (TEA) were found to enhance the chiral induction by  -cyclodextrin (-CD) in the reduction of acetophenone (ACPH) by aqueous NaBH4. The enantioselectivity obtained depends upon the molar ratio -CD:ACPH:TEA. Evidence for the formation of a three-component inclusion compound was obtained from detailled1H and2H NAM studies. The restriction of the molecular motion of the prochiral center probably accounts for the strong enhancement of the chiral induction observed. |
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