Palladium‐Catalyzed Chemo‐ and Enantioselective C−O Bond Cleavage of α‐Acyloxy Ketones by Hydrogenolysis | Zendy

Chen Jianzhong | Zendy; Zhang Zhenfeng | Zendy; Liu Delong | Zendy; Zhang Wanbin | Zendy

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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 .

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