A complementary method to obtain N-acyl enamides using the Heck reaction: extending the substrate scope for asymmetric hydrogenation |
| |
Authors: | Paul Harrison |
| |
Institution: | Dowpharma, Chirotech Technology Ltd, a subsidiary of The Dow Chemical Company, 321 Cambridge Science Park, Milton Road, Cambridge CB4 0WG, UK |
| |
Abstract: | 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. |
| |
Keywords: | N-Acyl enamides Heck reaction Asymmetric hydrogenation |
本文献已被 ScienceDirect 等数据库收录! |