The first organocatalytic asymmetric functionalization of aldehydes with a P-based compound has been successfully developed; the use of a simple chiral secondary amine has enabled the highly chemo- and enantioselective conjugate addition of diphenyl phosphine to α,β-unsaturated aldehydes, providing a direct route to chiral β-phosphine aldehyde intermediates. The synthetic utility of the asymmetric hydrophosphination (AHP) strategy was exemplified in a rapid one-pot (two step) synthesis of highly enantioenriched 1,3-aminophoshines, potentially useful P,N-ligands.
Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes / A. Carlone; G. Bartoli; M. Bosco; L. Sambri; P. Melchiorre. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - STAMPA. - 46:(2007), pp. 4504-4506. [10.1002/anie.200700754]
Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes
CARLONE, ARMANDO;BARTOLI, GIUSEPPE;BOSCO, MARCELLA;SAMBRI, LETIZIA;MELCHIORRE, PAOLO
2007
Abstract
The first organocatalytic asymmetric functionalization of aldehydes with a P-based compound has been successfully developed; the use of a simple chiral secondary amine has enabled the highly chemo- and enantioselective conjugate addition of diphenyl phosphine to α,β-unsaturated aldehydes, providing a direct route to chiral β-phosphine aldehyde intermediates. The synthetic utility of the asymmetric hydrophosphination (AHP) strategy was exemplified in a rapid one-pot (two step) synthesis of highly enantioenriched 1,3-aminophoshines, potentially useful P,N-ligands.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
