title: Preparation of chiral 3-arylpyrrolidines via the enantioselective 1,4-addition of arylboronic acids to fumaric esters catalyzed by Rh(I)/chiral diene complexes.
abstract: A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-tert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94→99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, No. 88, Section 4, Tingzhou Road, Taipei, 11677, Taiwan, Republic of China.
authors.forename: Yu-Chiang
authors.initials: YC
authors.lastname: Chung
authors.forename: Damodar
authors.initials: D
authors.lastname: Janmanchi
authors.forename: Hsyueh-Liang
authors.initials: HL
authors.lastname: Wu
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005650:Fumarates / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013386:Succinates / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D004952:Esters; D005650:Fumarates; D011759:Pyrrolidines; D013386:Succinates; D012238:Rhodium; C010686:benzeneboronic acid