Journal
TETRAHEDRON
Volume 61, Issue 26, Pages 6447-6459Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.03.110
Keywords
stereoselective synthesis; pyrrolidines; diastereoselectivity; palladium; arylhalide
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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.
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