Synlett 2010(1): 145-149  
DOI: 10.1055/s-0029-1218545
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Aziridination of Olefins Using a Chiral Sulfinamide as the Nitrogen Source

Vasco D. B. Bonifácioa, Concepción González-Bellob, Henry S. Rzepac, Sundaresan Prabhakar*a, Ana M. Lobo*a
a Chemistry Department, REQUIMTE/CQFB, and SINTOR-UNINOVA, Faculty of Sciences and Technology, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal
Fax: +351(21)2948550; e-Mail: aml@fct.unl.pt;
b Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
c Chemistry Department, Imperial College London, South Kensington Campus, Exhibition Road, London SW7 2AY, UK
Weitere Informationen

Publikationsverlauf

Received 28 July 2009
Publikationsdatum:
02. Dezember 2009 (online)

Zoom Image

Abstract

Chiral aziridination of cyclic α-bromoenones is achieved by the use of the lithium salt of (S S)-(+)-p-toluenesulfinamide, which leads to products with diastereomeric excesses in the range of 30-65% using a simple protocol. A key factor associated with chiral induction is the incorporation of the reacting olefin in a cycle, indicating the importance of conformational restriction in the reacting double bond.

Crossref Cited-by logo
Zitierungen