title: A Stereoselective Route to Tetrahydrobenzoxazepines and Tetrahydrobenzodiazepines via Ring-Opening and Aza-Michael Addition of Activated Aziridines with 2-Hydroxyphenyl and 2-Aminophenyl Acrylates.
abstract: A simple and efficient synthetic route to 2,3,4,5-tetrahydrobenzoxazepines and -benzodiazepines bearing easily functionalizable appendages has been developed by ring-opening of activated aziridines with 2-hydroxyphenyl acrylates and 2-aminophenyl acrylate, respectively, and subsequent intramolecular C-N bond formation through palladium-catalyzed aza-Michael reaction. The straightforward synthetic approach delivers the desired molecular scaffolds in high yields (up to 82%) with excellent stereoselectivity (ee up to 94%).
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Chandan Kumar
authors.initials: CK
authors.lastname: Shahi
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Aditya
authors.initials: A
authors.lastname: Bhattacharyya
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Yerramsetti
authors.initials: Y
authors.lastname: Nanaji
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Manas K
authors.initials: MK
authors.lastname: Ghorai