One-Pot, Fluoride-Promoted Wittig Reaction

被引：8

作者：

Fumagalli, Tiziano ^{[1
]}

Sello, Guido ^{[1
]}

Orsini, Fulvia ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 12期

关键词：

Tetra-n-butylammonium fluoride; -unsaturated compounds; Wittig reaction; STABILIZED PHOSPHORUS YLIDES; ALPHA; BETA-UNSATURATED ESTERS; (E)-ALPHA; STEREOSELECTIVE-SYNTHESIS; HIGH-PRESSURE; EFFICIENT CATALYST; ARYL IODIDES; LIGAND-FREE; HECK; REAGENTS;

D O I：

10.1080/00397910802654633

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, fluoride-promoted Wittig reaction was developed. The reactions of ethyl -bromoacetate with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced ,-unsaturated esters in good to excellent yields and E-stereoselectivity. Under the same conditions, reactions of ethyl -bromopropionate, -bromo acetonitrile, and -bromoacetophenone with aliphatic and aromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced the expected ,-unsaturated derivatives in good E-stereoselectivity. The protocol was extended to semistabilized ylides and applied to the synthesis of some combretastatin analogs.

引用

页码：2178 / 2195

页数：18

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