title: Synthesis of tetrahydropyridazines by a metal-carbene-directed enantioselective vinylogous N-H insertion/Lewis acid-catalyzed diastereoselective Mannich addition.
abstract: A versatile cascade of reactions, triggered by Rh(II)-catalyzed diazo decomposition followed by a vinylogous N-H insertion/Lewis acid catalyzed Mannich addition, that produces highly substituted 1,2,3,6-tetrahydropyridazines in up to 97 % ee with high yield and diastereocontrol has been developed.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
authors.forename: Xinfang
authors.initials: X
authors.lastname: Xu
authors.forename: Peter Y
authors.initials: PY
authors.lastname: Zavalij
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction / Q000379:methods; D058116:Lewis Acids / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D058116:Lewis Acids; D011724:Pyridazines; C030011:carbene; D012238:Rhodium; D008697:Methane