Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols

被引：179

作者：

Martinelli, MJ ^{[1
]}

Nayyar, NK ^{[1
]}

Moher, ED ^{[1
]}

Dhokte, UP ^{[1
]}

Pawlak, JM ^{[1
]}

Vaidyanathan, R ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Lilly Res Labs, Chem Proc R&D, Indianapolis, IN 46285 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol990658l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol, The alpha-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate, The role of the amine is discussed, in addition to catalyst requirements and solvent effects.

引用

页码：447 / 450

页数：4

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