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Ruthenium‐Catalyzed Enantioselective Hydrogenation/Lactonization of 2‐Acylarylcarboxylates: Direct Access to Chiral 3‐Substituted Phthalides
Author(s) -
Lu Bin,
Zhao Mengmeng,
Ding Guangni,
Xie Xiaomin,
Jiang Lili,
RatovelomananaVidal Virginie,
Zhang Zhaoguo
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700695
Subject(s) - synthon , enantioselective synthesis , ruthenium , catalysis , chemistry , combinatorial chemistry , benzene , tandem , molecule , organic chemistry , materials science , composite material
Highly enantioselective tandem hydrogenation/lactonization of various 2‐acylarylcarboxylates including 2‐aroylarylcarboxylates were realized by using [RuCl(benzene)( S )‐SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee ) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3‐substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram‐scale reaction was performed to further demonstrate the practicality of this approach.