title: Enantioselective and rapid Rh-catalyzed arylation of N-tosyl- and N-nosylaldimines in methanol.
abstract: Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-d-aspartate (NMDA) receptor.
authors.affiliation: Department of Chemistry and Instrumentation Center, National Taiwan Normal University , No. 88, Section 4, Tingzhou Road Taipei 11677, Taiwan, Republic of China.
authors.forename: Chun-Chih
authors.initials: CC
authors.lastname: Chen
authors.forename: Balraj
authors.initials: B
authors.lastname: Gopula
authors.forename: Jin-Fong
authors.initials: JF
authors.lastname: Syu
authors.forename: Jhih-Han
authors.initials: JH
authors.lastname: Pan
authors.forename: Ting-Shen
authors.initials: TS
authors.lastname: Kuo
authors.forename: Ping-Yu
authors.initials: PY
authors.lastname: Wu
authors.forename: Julian P
authors.initials: JP
authors.lastname: Henschke
authors.forename: Hsyueh-Liang
authors.initials: HL
authors.lastname: Wu
mesh_terms: D002384:Catalysis; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D016202:N-Methylaspartate / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D044005:Tetrahydroisoquinolines; D014105:Tosyl Compounds; C096775:1,2,3,4-tetrahydro-1-phenylisoquinoline; D016202:N-Methylaspartate; D012238:Rhodium; D000432:Methanol