Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

Ashley N Jarvis; Andrew B McLaren; Helen M I Osborn; Joseph Sweeney

doi:10.3762/bjoc.9.98

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines

Beilstein J Org Chem. 2013 May 2:9:852-9. doi: 10.3762/bjoc.9.98. Print 2013.

Authors

Ashley N Jarvis¹, Andrew B McLaren, Helen M I Osborn, Joseph Sweeney

Affiliation

¹ Department of Chemistry, University of Reading, Reading RG6 6AD, U. K.

Abstract

Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

Keywords: aziridines; catalytic; heterocycles; palladium; ring opening.