γ-hydroxy unsaturated nitriles:: Chelation-controlled conjugate additions

被引：13

作者：

Fleming, FF ^{[1
]}

Wang, QZ ^{[1
]}

Steward, OW ^{[1
]}

机构：

[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 10期

关键词：

D O I：

10.1021/ol005816j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Chelation between gamma-hydroxy unsaturated nitriles and Grignard reagents promotes an otherwise difficult anionic conjugate addition reaction. The intermediate chelate is readily generated by deprotonation with t-BuMgCl followed by the addition of a second Grignard reagent that triggers an intramolecular conjugate addition. Structurally diverse Grignard reagents add with equal efficiency, providing an intermediate anion that stereoselectively alkylates BnBr in an overall addition-alkylation reaction.

引用

页码：1477 / 1479

页数：3

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