Highly Diastereoselective Katsuki−Jacobsen Oxidation−Epoxidation of α-Silyloxy Sulfinyl Dienes: Synthetic Applications

Fernández de la Pradilla, Roberto; Castellanos, Alejandro; Osante, Iñaki; Colomer, Ignacio; Sánchez, Mateo I.

doi:10.1021/jo801803m.s004

jo801803m_si_004.pdf (4.51 MB)

Highly Diastereoselective Katsuki−Jacobsen Oxidation−Epoxidation of α-Silyloxy Sulfinyl Dienes: Synthetic Applications

journal contribution

posted on 2009-01-02, 00:00 authored by Roberto Fernández de la Pradilla, Alejandro Castellanos, Iñaki Osante, Ignacio Colomer, Mateo I. Sánchez

Katsuki−Jacobsen oxidation−epoxidation of acyclic α-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.