Chemistry of Ο-Silylated Ketene Acetals. Novel Chemical Transformation of Vinyl Sulfoxides and Related Sulfoxides

YASUYUKI KITA; OSAMU TAMURA; FUMIO ITOH; HITOSHI YASUDA; TAKASHI MIKI; YASUMITSU TAMURA

doi:10.1248/cpb.35.562

YASUYUKI KITA, OSAMU TAMURA, FUMIO ITOH, HITOSHI YASUDA, TAKASHI MIKI, YASUMITSU TAMURA

Author information

Keywords: Ο-methyl-Ο-tert-butyldimethylsilyl ketene acetal, vinyl sulfoxide, Michael-Pummerer-type reaction, methyl 4- (phenylthio) -4-siloxybutanoate, Ο-methyl-Ο-trimethylsilyl ketene acetal, double carbon-carbon bond forming reaction, dimethyl 3- (phenylthio) adipate

JOURNALS FREE ACCESS

Volume 35 (1987) Issue 2 Pages 562-569

DOI https://doi.org/10.1248/cpb.35.562

Details

Abstract

It is shown that vinyl sulfoxides undergo two novel modes of reactions induced selectively by the Ο-silylated ketene acetal used. Vinyl sulfoxides, on treatment with bulky tert-butyldimethylsilyl ketene acetals, undergo a Michael-Pummerer-type reaction to give γ-siloxy-γ- (phenylthio) esters, while with less bulky trimethylsilyl ketene acetals they undergo a double carbon-carbon bondforming reaction to give 3- (phenylthio) adipates. The reaction of related sulfoxides with Ο-silylated ketene acetals was also examined.

Released dates

Register with J-STAGE for free!