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Ru–Prolinamide‐Catalyzed Asymmetric Transfer Hydrogenation of Racemic β‐Heterosubstituted Cycloalkanones Driven by Dynamic Kinetic Resolution
Author(s) -
Vyas Vijyesh K.,
Bhanage Bhalchandra M.
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700688
Subject(s) - chemistry , kinetic resolution , ruthenium , substituent , transfer hydrogenation , catalysis , enantioselective synthesis , asymmetric hydrogenation , ligand (biochemistry) , aqueous solution , combinatorial chemistry , organic chemistry , biochemistry , receptor
A ruthenium–prolinamide catalytic system has been applied for the first time in dynamic kinetic resolution/asymmetric transfer hydrogenation reactions (DKR/ATH) in aqueous medium to synthesize cis ‐β‐heterosubstituted cycloalkanols with two contiguous chiral centers. The effect of various prolinamide ligands in DKR/ATH has been studied on different racemic‐β‐heterosubstituted cycloalkanones. A prolinamide ligand with a bulky substituent at an ortho position proves to be more effective than the previously reported ruthenium–TsDPEN catalytic system in aqueous medium, producing up to 99.1 % enantioselectivity and 99:1 diastereoselectivity.