title: Enantioselective Synthesis of N-H-Free 1,5-Benzothiazepines.
abstract: An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and α,β-unsaturated pyrazoleamides gave direct access to N-H-free 1,5-benzothiazepines in the presence of a chiral N,N'-dioxide/Yb(OTf)3complex. Excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 %) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(-)-Thiazesim.
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Guojin
authors.initials: G
authors.lastname: Wang
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P.R. China.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000577:Amides / Q000737:chemistry; D000814:Aniline Compounds; D000928:Antidepressive Agents / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry; D013237:Stereoisomerism; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C106746:1,5-benzothiazepine; D000577:Amides; D000814:Aniline Compounds; D000928:Antidepressive Agents; D011720:Pyrazoles; D013841:Thiazepines; C005464:2-aminothiophenol; C003436:thiazesim; D006859:Hydrogen; D009584:Nitrogen
keywords: Lewis acid catalysis; asymmetric catalysis; sulfa-Michael reaction; synthesis design; α,β-unsaturated pyrazolamide