title: Catalytic diastereoselective synthesis of diquinanes from acyclic precursors.
abstract: Upon exposure of up to 10 mol % tributylphosphine, electron-deficient 1,7-enynes undergo [3 + 2] cycloaddition to afford bicyclo[3:3:0] ring systems. In all but one case, products were obtained in >95:5 de, as determined by 1H NMR. This methodology enables concise and diastereoselective access to diquinane ring systems, whereby three contiguous stereogenic centers are set in a single manipulation.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, 78712, USA.
authors.forename: Jian-Cheng
authors.initials: JC
authors.lastname: Wang
authors.forename: Sze-Sze
authors.initials: SS
authors.lastname: Ng
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D007659:Ketones; D010720:Phosphines