Screening of chiral phosphines as catalysts for the enantioselective [3+2] annulations of N-tosylimines with allenic esters

The use of chiral, binaphthyl-based phosphepines as catalysts improves previous results for the enantioselective [3+2] cyclisation reactions between allenic esters and N-tosylimines, both in terms of conversion rate and enantioselectivity. Pyrrolines bearing 1-naphthyl, phenyl, o-tolyl and p-MeO-phenyl substituents on the stereogenic alpha-carbon have been obtained with enantiomeric excesses up to 64-80%. (c) 2007 Elsevier Ltd. All rights reserved.