期刊
TETRAHEDRON LETTERS
卷 52, 期 50, 页码 6682-6686出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.09.006
关键词
Friedel-Crafts alkylation; Lewis acid; Indole; Pyrrole; Ene reaction
资金
- Japan Science and Technology Agency (JST)
- Grants-in-Aid for Scientific Research [23750104] Funding Source: KAKEN
The chiral dicationic Pd complexes, bearing sterically demanding diphosphine ligands as Lewis acid catalysts, are shown to catalyze the asymmetric Friedel-Crafts (F-C) alkylations of indoles and pyrroles with beta,gamma-unsaturated alpha-ketoesters, to provide the F-C alkylation products with benzylic stereocenters in high yields and enantioselectivities. The reactive chelated structure, formed by the chiral dicationic Pd complex and the electrophile, would be important to gain a high level of asymmetric induction in the F-C alkylation. The F-C products can be readily functionalized to give alpha-hydroxy esters via catalytic asymmetric ene sequences. (C) 2011 Elsevier Ltd. All rights reserved.
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