title: Asymmetric Hydrogenation of Vinylthioethers: Access to Optically Active 1,5-Benzothiazepine Derivatives.
abstract: 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.
authors: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors: Wei
authors: W
authors: Li
authors: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors: Christoph
authors: C
authors: Schlepphorst
authors: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors: Constantin
authors: C
authors: Daniliuc
authors: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany. glorius@uni-muenster.de.
authors: Frank
authors: http://orcid.org/0000-0002-0648-956X
authors: F
authors: Glorius
mesh_terms: D004987:Ethers / Q000737:chemistry*; D006865:Hydrogenation; D013237:Stereoisomerism; D013841:Thiazepines / Q000737:chemistry*
chemical_list: C106746:1,5-benzothiazepine; D004987:Ethers; D013841:Thiazepines
keywords: 1,5-benzothiazepine; N-heterocyclic carbenes; asymmetric hydrogenation; ruthenium; vinylthioethers