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
收藏
页码：11071 / 11075
页数：5
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