Ru–Prolinamide‐Catalyzed Asymmetric Transfer Hydrogenation of Racemic β‐Heterosubstituted Cycloalkanones Driven by Dynamic Kinetic Resolution | Zendy

Vyas Vijyesh K. | Zendy; Bhanage Bhalchandra M. | Zendy

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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.

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