Anti-addition of Dimethylsulfoxonium Methylide to Acyclic α,β-Unsaturated Ketones and Its Application in Formal Synthesis of an Eicosanoid

Venkatachalam Angamuthu, Wen Jung Chang, Duen Ren Hou

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2 Scopus citations

Abstract

Cyclopropanation using dimethylsulfoxonium methylide (Corey-Chaykovsky reaction) was examined with a series of linear α,β-unsaturated ketones, and the results showed that the major trajectory for the addition of the sulfur ylide to the enones is anti, related to the γ-substituent. The stereochemical assignment for the generated cyclopropanes was achieved by X-ray crystallography or comparing with the reported spectroscopic data. We found that the diastereoselectivity was influenced by several factors, including the protecting groups, solvents, and temperatures, and good anti/syn ratios (>10:1) were often obtained using the tert-butyldimethylsilyl and tert-butyldiphenylsilyl-protected substrates. The method was applied to a formal synthesis of a natural eicosanoid with good efficiency.

Original languageEnglish
Pages (from-to)4088-4099
Number of pages12
JournalACS Omega
Volume2
Issue number8
DOIs
StatePublished - 31 Aug 2017

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