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
收藏
页码：2178 / 2195
页数：18
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