title: Rhodium/chiral diene complexes in the catalytic asymmetric arylation of β-pyrazol-1-yl acrylates.
abstract: The asymmetric conjugate addition of arylboronic acids to substituted and unsubstituted β-pyrazol-1-yl (E)-tert-butyl acrylates 4 catalyzed by 5 mol % of the Rh(I)/diene 2a catalyst provided the corresponding addition products in 44-98% yield and 91->99.5% ee. The method was applied to the formal synthesis of (3S)-3-aryl-3-(pyrazol-1-yl)propanoic acid 1b with agonistic activity toward the human GPR40 G-protein coupled receptor.
authors: Department of Chemistry and Instrumentation Center, National Taiwan Normal University , No. 88, Section 4, Tingzhou Road, Taipei 11677, Taiwan, Republic of China.
authors: Balraj
authors: B
authors: Gopula
authors: Yun-Fan
authors: YF
authors: Tsai
authors: Ting-Shen
authors: TS
authors: Kuo
authors: Ping-Yu
authors: PY
authors: Wu
authors: Julian P
authors: JP
authors: Henschke
authors: Hsyueh-Liang
authors: HL
authors: Wu
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D002384:Catalysis; D006801:Humans; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D043562:Receptors, G-Protein-Coupled / Q000819:agonists; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; C473034:FFAR1 protein, human; D011720:Pyrazoles; D043562:Receptors, G-Protein-Coupled; C031280:pyrazole; C522411:tert-butyl acrylate; D012238:Rhodium