title: Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines.
abstract: The reaction of racemic diarylmethylamines, (Ar(1)Ar(2)CHNR2), where Ar(1) is substituted with a 2-hydroxy group, with arylboroxines (Ar(3)BO)3 in the presence of a chiral diene-rhodium catalyst gave high yields of chiral triarylmethanes (Ar(1)Ar(2)CH*Ar(3)) with high enantioselectivity (up to 97% ee). The reaction is assumed to proceed through o-quinone methide intermediates which undergo Rh-catalyzed asymmetric 1,4-addition of the arylboron reagents.
authors.affiliation: †Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
authors.forename: Yinhua
authors.initials: Y
authors.lastname: Huang
authors.affiliation: †Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.|‡Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602, Singapore.
authors.forename: Tamio
authors.initials: T
authors.lastname: Hayashi
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000138:chemical synthesis* / Q000737:chemistry; D008744:Methylamines / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D006841:Hydrocarbons, Aromatic; D008744:Methylamines; C027451:methylamine; D012238:Rhodium; D008697:Methane