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Synthesis of Enantioenriched 5,6‐Dihydrophenanthridine Derivatives through retro‐Carbopalladation of Chiral o ‐Bromobenzylamines
Author(s) -
Ye Juntao,
Limouni Aurore,
Zaichuk Sonia,
Lautens Mark
Publication year - 2015
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.201411276
Subject(s) - enantioselective synthesis , aldimine , catalysis , chemistry , aryl , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
Retro‐carbopalladation of aldimines in the presence of a suitable β‐hydrogen atom has been observed in the Pd‐catalyzed homocoupling reactions of o ‐bromobenzylamines, providing an expeditious synthetic route to 5,6‐dihydrophenanthridine derivatives. Furthermore, a highly enantioselective synthesis of 6‐aryl‐substituted 5,6‐dihydrophenanthridines was achieved in a one‐pot manner by taking advantage of Rh and Pd catalysis.