Phosphane-Catalyzed [4+1] Annulation between Nitroalkenes and MoritaBaylis-Hillman Carbonates: Facile Synthesis of Isoxazoline N-Oxides by Phosphorus Ylides

被引：38
|
作者：
Zhou, Rong [1 ,2 ,3 ]
Duan, Chong [2 ,3 ]
Yang, Changjiang [2 ,3 ]
He, Zhengjie [2 ,3 ]
机构：
[1] Taiyuan Univ Technol, Coll Chem & Chem Engn, Taiyuan 030024, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
[3] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 04期
基金：
中国国家自然科学基金;
关键词：
annulation; isoxazolines; phosphanes; reaction mechanisms; ylides; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; SELECTIVE SYNTHESIS; DERIVATIVES; TANDEM; ESTERS; NITROACETATE; SUBSTITUENT;
D O I：
10.1002/asia.201301633
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A phosphane-catalyzed [4+1] annulation between nitroalkenes and Morita-Baylis-Hillman carbonates has been realized; this provides facile and diastereoselective access to polysubstituted isoxazoline N-oxides in moderate to excellent yields. In the annulation, an in situ formed allylic phosphorus ylide presumably serves as a pivotal active intermediate. This reaction accordingly represents the first example of phosphorus ylide initiated [4+1] cyclization of nitroalkenes to give isoxazoline N-oxides.
引用
收藏
页码：1183 / 1189
页数：7
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