Issue 10, 2015

Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel–Crafts type allylic alkylation of phenols

Abstract

Palladium-catalyzed asymmetric intramolecular Friedel–Crafts type allylic alkylation reaction of phenols was developed under mild conditions. In the presence of Pd2(dba)3 with (1R,2R)-DACH-phenyl Trost ligand (L2) in toluene at 50 °C, the reaction provides various C4 substituted tetrahydroisoquinolines with moderate to excellent yields, regioselectivity and enantioselectivity.

Graphical abstract: Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel–Crafts type allylic alkylation of phenols

Supplementary files

Article information

Article type
Paper
Submitted
10 Dec 2014
Accepted
19 Jan 2015
First published
20 Jan 2015

Org. Biomol. Chem., 2015,13, 3086-3092

Author version available

Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel–Crafts type allylic alkylation of phenols

Z. Zhao, Q. Xu, Q. Gu, X. Wu and S. You, Org. Biomol. Chem., 2015, 13, 3086 DOI: 10.1039/C4OB02574A

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