Tuesday, 24 May 2005

This presentation is part of: Organic Posters

“Instant methylide" modification of the Corey-Chaykovsky cyclopropanation reaction

James A. Ciaccio, Courtney E. Aman, and Shahrokh Saba. Fordham University, Bronx, NY

We recently reported that sulfoxonium and sulfonium methylides are generated upon treatment of storable, dry mixtures of Me3S(O)I/ KOt-Bu and Me3SI/NaH, respectively, with carbonyl compounds in DMSO to conveniently and rapidly afford the corresponding epoxides by the Corey-Chaykovsky reaction (Ciaccio et al., Synth. Commun. 2003, 33, 2135). Using mixtures of Me3S(O)I/ KOt-Bu and Me3S(O)I/ NaH under similar conditions, we now report that various a,b-unsaturated ketones afford the corresponding cyclopropyl ketones in good yields. This “instant methylide” modification of the Corey-Chaykovsky cyclopropanation reaction offers a convenient and experimentally simple preparation of cyclopropyl ketones, with advantages over conventional procedures: ease of handling (mixtures of sulfoxonium salt and base can be stored indefinitely under anhyd. conditions); in most cases, methylides are generated in the presence of the carbonyl substrate; reaction times are relatively short. Preliminary results suggest that aziridination of suitably substituted imines is possible.

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