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 / F. Pesciaioli; F. De Vincentiis; P. Galzerano; G. Bencivenni; G. Bartoli; A. Mazzanti; P. Melchiorre. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - ELETTRONICO. - 47:(2008), pp. 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.
2008
Organocatalytic Asymmetric Aziridination of Enones / F. Pesciaioli; F. De Vincentiis; P. Galzerano; G. Bencivenni; G. Bartoli; A. Mazzanti; P. Melchiorre. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - ELETTRONICO. - 47:(2008), pp. 8703-8706. [10.1002/anie.200803647]
F. Pesciaioli; F. De Vincentiis; P. Galzerano; G. Bencivenni; G. Bartoli; A. Mazzanti; P. Melchiorre
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/63929
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 16
  • Scopus 159
  • ???jsp.display-item.citation.isi??? 147
social impact