A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of r-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable R,R-disubstituted R-amino acid esters has been demonstrated.

Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center

DE FUSCO, CLAUDIA;FUOCO, TIZIANA;LATTANZI, Alessandra
2012

Abstract

A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of r-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable R,R-disubstituted R-amino acid esters has been demonstrated.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/3877465
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