Sequential cyclosulfonylation and alkylation as a versatile strategy for dihydropyran synthesis

被引：2

作者：

Edwards, GL ^{[1
]}

Sinclair, DJ ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

SYNTHESIS-STUTTGART | 2005年 / 20期

关键词：

sulfones; alkylations; heterocycles; enol ethers; alkyl halides;

D O I：

10.1055/s-2005-918498

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of 3,4-dihydro-6-(p-toluenesulfonyl-methyl)-2H-pyran (2) with n-BULi and alkylation of the lithiated allyl sulfone gives good to excellent yields of monoalkylated products 3. No gamma-substitution is observed in the monoalkylated products. A second deprotonation allows for the introduction of a second alkyl group. Desulfonylation can be effected with either sodium amalgam or sodium/ethanol in THF.

引用

页码：3613 / 3619

页数：7

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