Highly diastereoselective Katsuki-Jacobsen oxidation-epoxidation of alpha-silyloxy sulfinyl dienes: synthetic applications.
Katsuki-Jacobsen oxidation-epoxidation of acyclic alpha-silyloxy sulfinyl dienes, followed by acid-promoted cyclization, leads to 2,5-trans-sulfonyl dihydrofurans with good selectivities. As an application, the formal syntheses of (6S,7S,9R,10R)- and (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diols is reported.
Fernández de la Pradilla
Roberto
R
Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain. iqofp19@iqog.csic.es
Castellanos
Alejandro
A
Osante
Iñaki
I
Colomer
Ignacio
I
Sánchez
Mateo I
MI
D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D017646:Organosilicon Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
C445820:(2,3,5,10)-6,9-epoxynonadec-18-ene-7,10-diol; D000466:Alkadienes; D000475:Alkenes; D004852:Epoxy Compounds; D005663:Furans; D017646:Organosilicon Compounds; D013454:Sulfoxides