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Palladium(0)‐Catalyzed Enantioselective CH Arylation of Cyclopropanes: Efficient Access to Functionalized Tetrahydroquinolines
Author(s) -
Saget Tanguy,
Cramer Nicolai
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207959
Subject(s) - palladium , enantioselective synthesis , metalation , chemistry , combinatorial chemistry , catalysis , stereochemistry , organic chemistry
Activated : The title reaction proceeds efficiently with 1 mol % of palladium and gives tetrahydroquinolines in excellent enantioselectivities (see scheme). The enantiodiscriminating concerted metalation–deprotonation step occurs via a rare seven‐membered palladacycle. The cyclopropyl‐substituted tetrahydroquinolines can be regioselectively and enantiospecifically reduced to chiral tetrahydrobenzoazepines.