title: A Synthetic Route to Chiral Dihydrobenzothiazines through Ring Opening of Activated Aziridines with 2-Halothiophenols/Copper-Powder-Mediated C-N Cyclization.
abstract: A simple protocol for the synthesis of dihydrobenzothiazines through regio- and stereoselective S(N)2-type ring opening of N-tosylaziridines with sulfur nucleophiles followed by copper-powder-mediated intramolecular C-N cyclization in excellent yields (up to 95%) with high diastereo- and enantioselectivity (up to >99%) is reported.
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India. mkghorai@iitk.ac.in.
authors: Manas K
authors: MK
authors: Ghorai
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
authors: Masthanvali
authors: M
authors: Sayyad
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
authors: Yerramsetti
authors: Y
authors: Nanaji
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
authors: Sourita
authors: S
authors: Jana
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001388:Aziridines; D001555:Benzene Derivatives; D010636:Phenols; D013438:Sulfhydryl Compounds; D013843:Thiazines; D003300:Copper; C042983:thiophenol
keywords: asymmetric synthesis; aziridines; copper; regioselectivity; stereoselectivity