H-bonding additives act like Lewis acid catalysts

被引：427

作者：

Schreiner, PR

Wittkopp, A

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

[2] Univ Georgia, Dept Chem, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 02期

关键词：

D O I：

10.1021/ol017117s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A combination of NMR, IR, and ab initio techniques reveals the striking structural similarities of an exemplary H-bonded complex of an N-acyloxazolidinone with an N,N'-disubstituted electron-poor thiourea and the corresponding Lewis acid complex. Although the H-bond association constant is lower than for the Lewis acid adduct, Diels-Alder reactions are accelerated and stereochemically altered in a fashion similar to weak Lewis acids.

引用

页码：217 / 220

页数：4

共 25 条

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