Asymmetric Hydrogenation of Vinylthioethers: Access to Optically Active 1,5‐Benzothiazepine Derivatives | Zendy

Li Wei | Zendy; Schlepphorst Christoph | Zendy; Daniliuc Constantin | Zendy; Glorius Frank | Zendy

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Asymmetric Hydrogenation of Vinylthioethers: Access to Optically Active 1,5‐Benzothiazepine Derivatives

Author(s) -

Li Wei,

Schlepphorst Christoph,

Daniliuc Constantin,

Glorius Frank

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201512032

Subject(s) - stereocenter , asymmetric hydrogenation , optically active , combinatorial chemistry , ruthenium , enantioselective synthesis , chemistry , stereochemistry , organic chemistry , catalysis

A novel asymmetric hydrogenation of vinylthioethers was developed using a ruthenium(II) NHC complex. This method provides an efficient approach to optically active 1,5‐benzothiazepines featuring stereocenters with C−S bonds. Excellent enantioselectivities (up to 95 % ee ) and high yields (up to 99 %) were obtained for a variety of substrates bearing a range of useful functional groups. Moreover, this methodology could be directly applied to the synthesis of the antidepressant drug R ‐(−)‐thiazesim.

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