Catalytic Allylation of Stabilized Phosphonium Ylides with Primary Allylic Amines

被引：59

作者：

Ma, Xian-Tao ^{[1
]}

Wang, Yong ^{[1
]}

Dai, Rui-Han ^{[1
]}

Liu, Cong-Rong ^{[1
,2
]}

Tian, Shi-Kai ^{[1
,3
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Nanjing Inst Technol, Dept Environm Engn, Nanjing 211167, Jiangsu, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 21期

基金：

中国国家自然科学基金;

关键词：

C-N BONDS; WITTIG REACTION; OLEFINATION; ALKYLATION; ALDEHYDES; CLEAVAGE; CONSTRUCTION; ALLYLAMINES; MECHANISM; SECONDARY;

D O I：

10.1021/jo401736k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of ketone-stabilized phosphonium ylides were allylated with high regioselectivity by primary allylic amines in the presence of S mol % Pd(PPh3)(4) and 10 mol % B(OH)(3), and subsequent one-pot Wittig olefination gave structurally diverse alpha,beta-unsaturated ketones in good to excellent overall yields with excellent E selectivity. The one-pot allylation/olefination reaction was extended to ester- and nitrile-stabilized phosphonium ylides by replacing B(OH)(3) with TsOH, and the corresponding alpha,beta-unsaturated esters and nitriles were obtained in moderate overall yields.

引用

页码：11071 / 11075

页数：5

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