"Instant methylide" modification of the Corey-Chaykovsky epoxide synthesis
"Instant methylide" modification of the Corey-Chaykovsky epoxide synthesis
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DOI：
10.1081/scc-120021041
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发表时间：
2003-01-01
影响因子：
2.1
通讯作者：
Geneste, R
中科院分区：
文献类型：
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作者：
Ciaccio, JA;Drahus, AL;Geneste, R
我们报道了Me 3S（O）I-+（-）（1）和Me 3S +I-（2）分别与KOt-Bu和NaH形成稳定的干燥混合物，其在长时间储存（> 1年）后保持稳定。在添加羰基化合物的DMSO或DMSO/THF溶液时产生相应的亚甲基（Me 2SO = CH 2和Me 2S = CH 2），通过Corey-Chaykovsky反应以良好的产率和短的反应时间（当在50- 60 ℃下用1和KOt-Bu的混合物处理1-2 mmol的各种酮和醛时，短至20分钟）干净地提供环氧化物。
We report that Me3S(O)I-+(-) (1) and Me3S+I- (2) form stable, dry mixtures with KOt-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 when 1-2 mmol of various ketones and aldehydes were treated with a mixture of 1 and KOt-Bu at 50-60degreesC).