Journal
TETRAHEDRON LETTERS
Volume 45, Issue 50, Pages 9277-9280Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.10.063
Keywords
N-acyl enamides; Heck reaction; asymmetric hydrogenation
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A method to prepare N-acyl enamides is reported that is complementary to the existing protocols. Heck reaction of a variety of aryl trifluoromethanesulfonates with commercially available N-vinylacetamide occurred in a highly regioselective fashion to provide these valuable synthetic intermediates. This method permits the formation of N-acyl enamides containing functionality that would not be tolerated by the existing methods. Asymmetric hydrogenation using [diphosphine RhCOD]BF4 complexes provided optically active protected amines in up to 99% ee. De-acylation occurs without affecting the amine enantiopurity. (C) 2004 Elsevier Ltd. All rights reserved.
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