title: Tetrahydroquinolines and benzazepines through catalytic diastereoselective formal [4 + 2]-cycloaddition reactions between donor-acceptor cyclopropenes and imines.
abstract: Regio- and diastereoselective Lewis acid catalyzed cycloaddition reactions between imines and donor-acceptor cyclopropenes generated from silyl-protected enoldiazoacetates provide direct access to stable cyclopropane-fused tetrahydroquinolines and, with cyclopropane ring opening under mild conditions, to 1H-benzazipine derivatives.
authors.affiliation: Department of Chemistry & Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Phong M
authors.initials: PM
authors.lastname: Truong
authors.forename: Michael D
authors.initials: MD
authors.lastname: Mandler
authors.forename: Peter Y
authors.initials: PY
authors.lastname: Zavalij
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D001552:Benzazepines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001552:Benzazepines; D003521:Cyclopropanes; D007097:Imines; D011804:Quinolines; C030797:cyclopropane; C542964:1,2,3,4-tetrahydroquinoline