title: Highly enantioselective catalytic cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinolines and terminal alkynes.
abstract: The first catalytic asymmetric cross-dehydrogenative coupling of cyclic carbamates and terminal alkynes has been established. The reaction features high enantiocontrol and excellent functional group tolerance and displays a wide range of structurally and electronically diverse carbamates as well as terminal alkynes. N-Acyl hemiaminals were identified as the reactive intermediates through preliminary control experiments. Employing readily removable carbamates as substrates rather than traditionally adopted N-aryl amines allows applications in complex molecule synthesis and therefore advances the C-H functionalization strategy to a synthetically useful level.
authors.affiliation: †Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. China.
authors.forename: Shutao
authors.initials: S
authors.lastname: Sun
authors.affiliation: †Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. China.
authors.forename: Chengkun
authors.initials: C
authors.lastname: Li
authors.affiliation: §Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
authors.affiliation: †Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. China.
authors.forename: Hongxiang
authors.initials: H
authors.lastname: Lou
authors.affiliation: †Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. China.
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; D002219:Carbamates; D044005:Tetrahydroisoquinolines