This work was supported by the DGES of the Spanish Ministerio de Ciencia y Tecnología (PB97–0123 and BQU2001–0724-C02-) and by Generalitat Valenciana (CTIOIB/2002/320). A.B. also thanks Generalitat Valenciana for a predoctoral fellowship.
Enantioselective Synthesis of Cyanohydrin O-Phosphates Mediated by the Bifunctional Catalyst Binolam–AlCl†
Article first published online: 10 JUL 2003
Copyright © 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 42, Issue 27, pages 3143–3146, July 14, 2003
How to Cite
Baeza, A., Casas, J., Nájera, C., Sansano, J. M. and Saá, J. M. (2003), Enantioselective Synthesis of Cyanohydrin O-Phosphates Mediated by the Bifunctional Catalyst Binolam–AlCl. Angew. Chem. Int. Ed., 42: 3143–3146. doi: 10.1002/anie.200351552
- Issue published online: 10 JUL 2003
- Article first published online: 10 JUL 2003
- Manuscript Received: 2 APR 2003
- asymmetric catalysis;
- homogeneous catalysis;
(R)- and (S)-binolam–AlCl complexes act as bifunctional catalysts to mediate the enantioselective cyanophosphorylation of aldehydes at room temperature. The resulting chiral cyanohydrin O-phosphates can be reduced to β-aminoalcohols or, when suitably substituted, can be transformed into γ-cyanoallylic alcohols through palladium-catalyzed allylic substitution, without loss of enantiomeric excess (see scheme).