Wittig-type olefination catalyzed by PEG-telluride

被引：72

作者：

Huang, ZZ ^{[1
]}

Ye, S ^{[1
]}

Xia, W ^{[1
]}

Yu, YH ^{[1
]}

Tang, Y ^{[1
]}

机构：

[1] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 09期

关键词：

D O I：

10.1021/jo025586h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Soluble poly(ethylene glycol) (PEG)-supported telluride 2 was designed and synthesized for catalytic Wittig-type reactions. It was found that the catalytic loading could be reduced from 20 to 2 mol% by the introduction of PEG (even to 0.5 mol% when some telluride salts were used as the catalyst). Under the catalytic reaction conditions, a wide variety of aldehydes with different structures could react with bromoacetate to afford beta-substitutited or alpha,beta-disubstituted unsaturated esters in high yields with excellent E-stereoselectivity. The modified process, by using sodium bisulfite instead of triphenyl phosphite, represented a very simple product isolation procedure. The roles of PEG for promoting the ylide formation and stabilizing the catalytic species were disclosed. The mechanism was also studied.

引用

页码：3096 / 3103

页数：8

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