title: Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.
abstract: The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization mechanism. Mechanistic studies suggest formation of an allene intermediate, which undergoes hydroamination to generate allylic amines instead of the enamine or imine products typically observed in alkyne hydroaminations.
authors.affiliation: Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, California 92697, United States.
authors.forename: Qing-An
authors.initials: QA
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, California 92697, United States.
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, California 92697, United States.
authors.forename: Vy M
authors.initials: VM
authors.lastname: Dong
mesh_terms: D000143:Acids / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007211:Indoles / Q000737:chemistry*; D007700:Kinetics; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000143:Acids; D000466:Alkadienes; D000480:Alkynes; D000588:Amines; D007211:Indoles; D008024:Ligands; C025947:propadiene; D002244:Carbon; D012238:Rhodium; D009584:Nitrogen