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

The stereoselective synthesis of N-acyl-and N-Boc-protected pyrrolidines via Pd-catalyzed reactions of gamma-(N-acylamino) alkenes and gamma-(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 gamma-(N-arylamino) alkenes, these transform at ions proceed in high yield and high regioselectivity with both electron-rich and electron-deficient aryl bromides as well as vinyl bromide substrates. (c) 2005 Elsevier Ltd. All rights reserved.