Instant methylide modification of the Corey-Chaykovsky epoxide synthesis

被引：29

作者：

Ciaccio, JA ^{[1
]}

Drahus, AL ^{[1
]}

Meis, RM ^{[1
]}

Tingle, CT ^{[1
]}

Smrtka, M ^{[1
]}

Geneste, R ^{[1
]}

机构：

[1] Fordham Univ, Dept Chem, Bronx, NY 10458 USA

来源：

SYNTHETIC COMMUNICATIONS | 2003年 / 33卷 / 12期

关键词：

epoxide synthesis; Corey-Chaykovsky reaction; sulfurylide;

D O I：

10.1081/SCC-120021041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

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收藏

页码：2135 / 2143

页数：9

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