Diastereoselective Synthesis of α-Stabilized Phosphorus Ylides via a Four-Component Reaction

被引：6

作者：

Alizadeh, Abdolali ^{[1
]}

Zohreh, Nasrin ^{[1
]}

Zhu, Long-Guan ^{[2
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran 18716, Iran

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2009年 / 03期

关键词：

alpha-stabilized phosphorus ylide; triphenylphosphine; diketene; dialkyl acetylenedicarboxylate; multicomponent reaction; diastereoselective reaction; ONE-POT SYNTHESIS; WITTIG-REACTION; ALLENIC ESTERS; DERIVATIVES; ALLENECARBOXYLATES; STEREOCHEMISTRY; ACIDS; CHLORIDES; DIKETENE;

D O I：

10.1055/s-0028-1083315

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Functionalized and alpha-stabilized derivatives of dialkyl 2{1-[(alkylamino)carbonyl]-2-oxopropyl}-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene)succinate were obtained in excellent yields from the reaction between primary amines, diketene, and dialkyl acetylenedicarboxylate in the presence of triphenylphosphine. Not only the reaction is diastereoselective but also the formed diasteromer has two rotamers that are in equilibrium with each other. (1)H, (13)C, and (31)P NMR showed only one of the two rotamers and thus conversion of Z-isomer into another is negligible at room temperature.

引用

页码：464 / 468

页数：5

共 37 条

[1]

ALIZADEH A, 2008, SYNTHESIS-STUTTGART, P2076

[2]

A one-pot synthesis of 1,2-dihydroisoquinoline derivatives from isoquinoline via a four-component reaction [J].