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.
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.File in questo prodotto:
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