trans-Diastereoselective Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of α-Acetamido Benzocyclic Ketones via Dynamic Kinetic Resolution | Zendy

Andrej Emanuel Cotman | Zendy; Matic Lozinšek | Zendy; Baifan Wang | Zendy; Michel Stephan | Zendy; Barbara Mohar | Zendy

Open Access

trans-Diastereoselective Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of α-Acetamido Benzocyclic Ketones via Dynamic Kinetic Resolution

Author(s) -

Andrej Emanuel Cotman,

Matic Lozinšek,

Baifan Wang,

Michel Stephan,

Barbara Mohar

Publication year - 2019

Publication title -

organic letters

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b01069

Subject(s) - chemistry , kinetic resolution , catalysis , transfer hydrogenation , kinetic energy , ruthenium , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , physics , quantum mechanics

A highly efficient enantio- and diastereoselective catalyzed asymmetric transfer hydrogenation via dynamic kinetic resolution (DKR-ATH) of α,β-dehydro-α-acetamido and α-acetamido benzocyclic ketones to ent- trans-β-amido alcohols is disclosed employing a new ansa-Ru(II) complex of an enantiomerically pure syn- N, N-ligand, i.e. ent- syn-ULTAM-(CH 2 ) 3 Ph. DFT calculations of the transition state structures revealed an atypical two-pronged substrate attractive stabilization engaging the commonly encountered CH/π electrostatic interaction and a new additional O═S═O···HNAc H-bond hence favoring the trans-configured products.

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