Phosphine-Promoted Tandem Intermolecular Diels-Alder Reactions with Pentadienyl 4-Nitrobenzoate as a Diene Precursor

被引：3
|
作者：
Zhang, Le [1 ]
Liu, Ye [1 ]
Li, Chao-Xu [1 ]
Zhu, Lei [2 ]
Xiong, Guo-Yin [1 ]
Fan, Shi-Lu [1 ]
Dai, Jian-Jun [1 ]
Xiao, Hua [1 ,2 ]
机构：
[1] Hefei Univ Technol, Sch Food & Biol Engn, Hefei 230601, Peoples R China
[2] Hubei Engn Univ, Sch Chem & Mat Sci, Hubei Key Lab Qual Control Characterist Fruits &, Xiaogan 432000, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 35期
基金：
中国国家自然科学基金;
关键词：
MALEIMIDES;
D O I：
10.1021/acs.orglett.3c02209
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A phosphine-promoted tandem Diels-Alder reaction using pentadienyl 4-nitrobenzoate (a-vinyl MBH adduct) as a diene precursor with 3-olefinic oxindoles or CF3-activated ketones as dienophiles has been developed. The reaction proceeds through the formation of a pentadienyl phosphonium intermediate via S(N)2?addition, which acts as both a D-A diene and a precursor for the exomethylene moiety. This method offers a metal-free and step-efficient approach for synthesizing exomethylene-bearing spirooxindoles and dihydropyrans, which are privileged structures found in natural products.
引用
收藏
页码：6506 / 6510
页数：5
相关论文
共 50 条
12345