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Palladium‐Catalyzed Chemo‐ and Enantioselective C−O Bond Cleavage of α‐Acyloxy Ketones by Hydrogenolysis
Author(s) -
Chen Jianzhong,
Zhang Zhenfeng,
Liu Delong,
Zhang Wanbin
Publication year - 2016
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.201603590
Subject(s) - hydrogenolysis , chemistry , enantioselective synthesis , palladium , catalysis , bond cleavage , cleavage (geology) , kinetic resolution , alkyl , medicinal chemistry , organic chemistry , stereochemistry , geotechnical engineering , fracture (geology) , engineering
A chemoselective C−O bond cleavage of the ester alkyl side‐chain of α‐acyloxy ketones was realized for the first time by a highly efficient palladium‐catalyzed hydrogenolysis (S/C=6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of α‐acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99 % ee .