title: Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: formal synthesis of (S)-SKF 38393.
abstract: An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing β,β-diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.
authors.affiliation: Department of Chemistry and Instrumentation Center, Department of Chemistry, National Taiwan Normal University , No. 88, Section 4, Tingzhou Road Taipei 11677, Taiwan, Republic of China , and ScinoPharm Taiwan, No. 1, Nan-Ke eighth-Road Taiwan Science-Based Industrial Park, Shan-Hua, Tainan County, 74144, Taiwan, Republic of China.
authors.forename: Kung-Chih
authors.initials: KC
authors.lastname: Huang
authors.forename: Balraj
authors.initials: B
authors.lastname: Gopula
authors.forename: Ting-Shen
authors.initials: TS
authors.lastname: Kuo
authors.forename: Chien-Wei
authors.initials: CW
authors.lastname: Chiang
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: D015647:2,3,4,5-Tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001897:Boronic Acids; D009574:Nitro Compounds; D015647:2,3,4,5-Tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine; D012238:Rhodium