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Stereoarrayed CF 3 ‐Substituted 1,3‐Diols by Dynamic Kinetic Resolution: Ruthenium(II)‐Catalyzed Asymmetric Transfer Hydrogenation
Author(s) -
Cotman Andrej Emanuel,
Cahard Dominique,
Mohar Barbara
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600812
Subject(s) - ruthenium , transfer hydrogenation , kinetic resolution , chemistry , triethylamine , formic acid , catalysis , yield (engineering) , medicinal chemistry , alcohol , noyori asymmetric hydrogenation , enantioselective synthesis , combinatorial chemistry , organic chemistry , materials science , metallurgy
CF 3 ‐substituted 1,3‐diols were stereoselectively prepared in excellent enantiopurity and high yield from CF 3 ‐substituted diketones by using an ansa‐ruthenium(II)‐catalyzed asymmetric transfer hydrogenation in formic acid/triethylamine. The intermediate mono‐reduced alcohol was also obtained in very high enantiopurity by applying milder reaction conditions. In particular, CF 3 C(O)‐substituted benzofused cyclic ketones underwent either a single or a double dynamic kinetic resolution during their reduction.