Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-( N-acylamino) alkenes and γ-( N-Boc-amino) alkenes with aryl bromides

Abstract

The stereoselective synthesis of N-acyl- and N-Boc-protected pyrrolidines via Pd-catalyzed reactions of γ-( N-acylamino) alkenes and γ-( N-Boc-amino) alkenes with aryl bromides is described. These reactions effect formation of two bonds in a single operation and proceed with generally high levels of diastereoselectivity. In contrast to previously described reactions of γ-( N-arylamino) alkenes, these transformations proceed in high yield and high regioselectivity with both electron-rich and electron-deficient aryl bromides as well as vinyl bromide substrates.