Stereoselective synthesis of monofluoroalkyl α,β-unsaturated ketones from allenyl carbinol esters mediated by gold and Selectfluor.
Allenyl carbinol ester 3 isomerizes to an E,Z mixture of the corresponding diene 2 in the presence of gold catalyst 4, but the resulting mixture yields monofluoroalkyl α,β-unsaturated ketone 1 with exclusive E selectivity and in high yields after reaction with Selectfluor.
Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.
Zhuang
Z
Jin
Rachel S
RS
Hidinger
Bo
B
Xu
Gerald B
GB
Hammond
D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003979:Diazonium Compounds; D004952:Esters; D007659:Ketones; C408750:selectfluor; D006046:Gold