✍ Scribed by Manat Pohmakotr; Jirakorn Thisayukta
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rx-Chloro-cz-(phenylthio)cyclopropane and tx-acetoxy-a-(phenylthio)cyclopropanewere found to react with the silyl enol ethers of some ketones in the presence of Lewis acid in dichlorometharre to provide a-(phenykhio)cyclopropyl ketones,whichwere subjectedto reductionwith Ra-Ni to give the corresponding&cycIopropylketones. @ 1997Elsevier ScienceLtd.
Few methods for cc-cyclopropylation of crtrbonyl compounds and esters have appeared in the literatures, which involve the reactions of (n-allyl)palladium complexes with enolate anions of carbonyl compounds andesters.z-q Lackof such general methods prompted us to search for a new entry to ~cyclopropyl carbonyl compounds. By taking advantage of twlkylthioalkylation methods based on the reactions of tx-thiosubstituted electrophiles with silyl enol ethers or esters,5 we studied the possibilities of generating cyclopropyl thionium ion intermediate 26 from tx-chloro and a-acetoxy (phenylthio)cyclopropanes la7 and Ibs,s and its reaction with silyl enol ethers 3 expecting to obtain the desired a-(phenylthio)cyclopropyl ketones 4.
📜 SIMILAR VOLUMES
Stereospecific 1,2-rearrangement of cyclopropyl group is described as an efficient route to stereo-defined a-cyclopropyl ketones and cr-cyclopropyl aldols. Acceleration of the reaction by the introduction of trimethylsilyl (TMS) group to the a-position of cyclopropyl group is also noted. ## Cyclop