Journal
TETRAHEDRON
Volume 63, Issue 35, Pages 8563-8570Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.04.097
Keywords
asymmetric synthesis; allylic amination; palladium; monodentate phosphoramidite; alkaloid; tetrahydroisoquinoline
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Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl) prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96% ee) and 100% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest. (c) 2007 Elsevier Ltd. All rights reserved.
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