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Diastereoselective oxidation of sulfides to sulfoxides with potassium peroxymonosulfate

✍ Scribed by George J. Quallich; J. William Lackey

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 153 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97444-6

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✦ Synopsis

Potassium peroxymonosulfate oxidation of suffides to suffoxides occurs with high diastereosebctivky. In seeking a preparative process for the skfe chain of antibacterial CP-70,429, penem 1. we prepared the sulfoxkle side chain a as a 4:l mixture of ~6~6 and & sulfoxides by oxkfatbn of the sulfide 2 with mchlompemxybenzob acid.1 Chromatography was required to obtain the desired BQ,~Q suffoxkfe & Significant improvement in the diastereoselectivfty of the oxidatbn was sougM to improve the yield and eliminate the chromatography. TsOue c S-T&)llll c % CO,Na

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