Synthesis of Enantioenriched 5,6‐Dihydrophenanthridine Derivatives through retro‐Carbopalladation of Chiral  o ‐Bromobenzylamines | Zendy

Ye Juntao | Zendy; Limouni Aurore | Zendy; Zaichuk Sonia | Zendy; Lautens Mark | Zendy

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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.

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