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Rhodium‐Catalyzed ortho ‐Olefination of Sterically Demanding Benzamides: Application to the Asymmetric Synthesis of Axially Chiral Benzamides
Author(s) -
Yoshimura Ryo,
Tanaka Ken
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000797
Subject(s) - rhodium , steric effects , axial symmetry , catalysis , chemistry , combinatorial chemistry , organic chemistry , mathematics , geometry
It has been established that an unsubstituted cyclopentadienyl rhodium(III) (CpRh III ) complex is a highly active catalyst for the aerobic oxidative ortho C−H bond olefination of sterically demanding ortho ‐substituted benzamides with alkenes. This catalysis was successfully applied to the diastereoselective synthesis of axially chiral N , N ‐dialkylbenzamides. The combination of the ruthenium(II)‐catalyzed enantioselective hydrogenation and the CpRh III ‐catalyzed diastereoselective ortho C−H bond olefination enabled the asymmetric synthesis of axially chiral N , N ‐dialkylbenzamide derivatives with high ee values.