we have reported an asymmetric amine conjugate addition to enones that provides a suitable platform for developing an unprecedented example of highly chemoand stereoselective aziridinations of both linear and cyclic a,b-unsaturated ketones. The method,which affords valuable N-Cbz- as well as N-Boc-protected aziridines with almost complete diastereocontrol and very high enantioselectivity (up to 99%ee), exploits the ability of the readily available chiral primary amine catalyst salt 1 to promote a domino iminium–enamine intramolecular sequence.
F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, et al. (2008). Organocatalytic Asymmetric Aziridination of Enones. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 47, 8703-8706 [10.1002/anie.200803647].
Organocatalytic Asymmetric Aziridination of Enones
PESCIAIOLI, FABIO;DE VINCENTIIS, FRANCESCO;GALZERANO, PATRIZIA;BENCIVENNI, GIORGIO;BARTOLI, GIUSEPPE;MAZZANTI, ANDREA;MELCHIORRE, PAOLO
2008
Abstract
we have reported an asymmetric amine conjugate addition to enones that provides a suitable platform for developing an unprecedented example of highly chemoand stereoselective aziridinations of both linear and cyclic a,b-unsaturated ketones. The method,which affords valuable N-Cbz- as well as N-Boc-protected aziridines with almost complete diastereocontrol and very high enantioselectivity (up to 99%ee), exploits the ability of the readily available chiral primary amine catalyst salt 1 to promote a domino iminium–enamine intramolecular sequence.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
