Catalytic diastereoselective synthesis of diquinanes from acyclic precursors.
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.
Wang
Jian-Cheng
JC
Department of Chemistry and Biochemistry, University of Texas at Austin, 78712, USA.
Ng
Sze-Sze
SS
Krische
Michael J
MJ
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
D000475:Alkenes; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D007659:Ketones; D010720:Phosphines