A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.
One-pot synthesis of chiral multifunctionalized aziridines / Fioravanti, Stefania; Sara, Morea; Morreale, Alberto; Pellacani, Lucio; Tardella, Paolo Antonio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:2(2009), pp. 484-488. [10.1016/j.tet.2008.11.017]
One-pot synthesis of chiral multifunctionalized aziridines
FIORAVANTI, Stefania;MORREALE, Alberto;PELLACANI, Lucio;TARDELLA, Paolo Antonio
2009
Abstract
A direct synthetic procedure to obtain chiral aziridines is reported, involving a diastereoselective aza-MIRC (Michael Initiated Ring Closure) reaction. Multifunctionalized aziridines are obtained in high overall yields (82-92%) and with a diastereomeric ratio up to 99:1. Further synthetic elaboration can lead to the formation of interesting biochemical molecules, such as amino glycosides. The diastereomeric induction seems to be strongly controlled both by the choice of chiral moiety and by the electron withdrawing groups (EWG) present on the starting alkenes. (C) 2008 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
