title: Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D.
abstract: Bis-heteroaryl or bis-aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.
authors.affiliation: Department of Chemistry, University of Houston, 112 Fleming Building, Houston, TX 77204-5003 (USA).
authors.forename: Jiun-Le
authors.initials: JL
authors.lastname: Shih
authors.affiliation: Department of Chemistry, University of Houston, 112 Fleming Building, Houston, TX 77204-5003 (USA).
authors.forename: Thien S
authors.initials: TS
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, University of Houston, 112 Fleming Building, Houston, TX 77204-5003 (USA). jmay@uh.edu.
authors.forename: Jeremy A
authors.initials: JA
authors.lastname: May
mesh_terms: D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001713:Biphenyl Compounds; D006575:Heterocyclic Compounds, 3-Ring; D009281:Naphthalenes; D011760:Pyrrolidinones; C475744:S(-)2,2'-dihydroxy-1,1'-binaphthyl; C587607:discoipyrrole D
keywords: bis-aryl stereocenters; enantioselective catalysis; heterocycles; organocatalysis; trifluoroborate salts