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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.