Enantioselective Additive Pummerer-Type Rraction in Chiral, Non-racemic Vinyl Sulfoxides Induced by O-Silylated Ketene Acetal

Norio SHIBATA; Chino FUJIMORI; Shigekazu FUJITA; Yasuyuki KITA

doi:10.1248/cpb.44.892

Norio SHIBATA, Chino FUJIMORI, Shigekazu FUJITA, Yasuyuki KITA

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Keywords: O-methyl-O-tert-butyldimethylsilyl ketene acetal, additive Pummerer reaction, vinyl sulfoxide, enantioselective reaction methyl 4-siloxy-4-sufenylbutyrate

JOURNAL FREE ACCESS

1996 Volume 44 Issue 5 Pages 892-894

DOI https://doi.org/10.1248/cpb.44.892

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Abstract

Treatment of chiral, non-racemic vinyl sulfoxides with O-silylated ketene acetal in the presence of a catalytic amount of zinc chloride in tetrahydrofuran resulted in an enantioselective Pummerer-type reaction, affording a considerable yield of the corresponding enantiomerically enriched methyl 4-siloxy-4-sulfenylbutyrate in 78-82% ee.

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