The highly enantioselective organocatalytic β-hydroxylation of α,β-unsaturated ketones has been accomplished using oximes as the oxygen-centered nucleophile. Optically active products are obtained with enantioselectivity up to 94%. Central to these studies has been the use of the catalytic primary amine salt A, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium-ion catalysis with enones.
A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, et al. (2007). Organocatalytic Asymmetric β -Hydroxylation of alfa ,beta -Unsaturated Ketones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 5492-5495.
Organocatalytic Asymmetric β -Hydroxylation of alfa ,beta -Unsaturated Ketones
CARLONE, ARMANDO;BARTOLI, GIUSEPPE;BOSCO, MARCELLA;PESCIAIOLI, FABIO;SAMBRI, LETIZIA;MELCHIORRE, PAOLO
2007
Abstract
The highly enantioselective organocatalytic β-hydroxylation of α,β-unsaturated ketones has been accomplished using oximes as the oxygen-centered nucleophile. Optically active products are obtained with enantioselectivity up to 94%. Central to these studies has been the use of the catalytic primary amine salt A, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium-ion catalysis with enones.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
