Catalytic asymmetric (4+1) annulation of nitroalkenes with allylic acetates: stereoselective synthesis of isoxazoline N-oxides

被引：10
作者：
Luo, Jinghua [1 ]
Chen, Rongshun [2 ]
Fan, Xia [1 ]
Gong, Junyu [1 ]
Han, Jie [1 ]
He, Zhengjie [1 ,3 ]
机构：
[1] Nankai Univ, Chem Coll, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Jiangsu, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 29期
基金：
中国国家自然科学基金;
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; BAYLIS-HILLMAN CARBONATES; DIASTEREOSELECTIVE SYNTHESIS; AMMONIUM YLIDES; CYCLIZATION; CYCLOPROPANATION; DERIVATIVES; ALCOHOLS; TANDEM; PHASE;
D O I：
10.1039/c9ob01058k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric (4 + 1) annulation of alpha-nitro cinnamates with Morita-Baylis-Hillman (MBH) acetates catalyzed by alpha-isocupreine is reported. It provides chiral isoxazoline N-oxides in moderate to good yields with 88-99% ee, and represents the first catalytic asymmetric (4 + 1) annulation of activated nitroalkenes with in situ generated ammonium ylides. It also affords a practical and efficient access to chiral isoxazoline N-oxides.
引用
收藏
页码：6989 / 6993
页数：5
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