“Instant Methylide” Modification of the Corey–Chaykovsky Epoxide Synthesis
…, RM Meis, CT Tingle, M Smrtka, R Geneste
Index: Ciaccio, James A.; Drahus, Antoinette L.; Meis, Regina M.; Tingle, Carice T.; Smrtka, Michael; Geneste, Richard Synthetic Communications, 2003 , vol. 33, # 12 p. 2135 - 2143
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Citation Number: 37
Abstract
Abstract We report that Me3S (O)+ I−(1) and Me3S+ I−(2) form stable, dry mixtures with KO t- Bu and NaH, respectively, which remain stable upon prolonged storage (> 1 year). The corresponding methylides (Me2SO= CH2 and Me2S= CH2) are generated upon addition of DMSO or DMSO/THF solutions of carbonyl compounds, cleanly affording epoxides via the Corey–Chaykovsky reaction in good yields and short reaction times (as short as 20 min ...
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