Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.
A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT(1A) receptor antagonist was synthesized efficiently using this method.
Miao
Lei
L
Department of Chemistry, The University at Buffalo, The State University of New York, Buffalo, New York 14260, United States.
Haque
Imranul
I
Manzoni
Maria R
MR
Tham
Weng Siong
WS
Chemler
Sherry R
SR
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D007211:Indoles; D002244:Carbon; D003300:Copper; D006859:Hydrogen; D001554:Benzene