title: Rhodium-catalyzed asymmetric arylation of cyclic N-sulfonyl aryl alkyl ketimines: efficient access to highly enantioenriched α-tertiary amines.
abstract: A simple catalyst system of Rh(I)/sulfur-olefin with exceptional catalytic performance has been developed for the highly enantioselective arylation of cyclic N-sulfonyl aryl alkyl ketimines with arylboroxines/arylboronic acids. Optically active α-arylalkyl-substituted benzosultams and benzosulfamidates which are generally difficult to obtain were easily prepared with excellent stereocontrol (up to 99.9% ee). The synthetic utility of the approach was demonstrated by the facile construction of NMDA antagonist FR115427 and benzoxazinone derivatives. This protocol offers new opportunities for the efficient synthesis of diverse chiral α-tertiary amines.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road, Shanghai 201203, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Jiang
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D016202:N-Methylaspartate / Q000037:antagonists & inhibitors; D012238:Rhodium / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000588:Amines; D013450:Sulfones; D044005:Tetrahydroisoquinolines; C084456:1-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline; D016202:N-Methylaspartate; D012238:Rhodium