P(NMe2)3-Mediated Reductive (1+4) Annulation Reaction of α-Keto Esters with Nitroalkenes: A Facile Synthesis of Polysubstituted Isoxazoline N-Oxides

被引：2
|
作者：
Liu, Yiyi [1 ]
Lu, Kanghui [2 ,3 ]
Wan, Tao [1 ]
Wei, Jiaqiang [1 ]
Wu, Junjie [1 ]
Gong, Shangkun [1 ]
Xu, Song [1 ]
He, Zhengjie [2 ,3 ]
机构：
[1] State Grid Hunan Elect Power Corp Ltd Res Inst, Changsha 410007, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 100193, Peoples R China
[3] Nankai Univ, Coll Chem, Tianjin 100193, Peoples R China
来源：
CHEMISTRYSELECT | 2021年 / 6卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Five-membered cycles; Kukhtin-Ramirez adducts; (1+4) Annulation reactions; α -keto esters; Synthetic methods; DIASTEREOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; TANDEM; CONDENSATION; ISATINS; 1,2-DICARBONYLS; DERIVATIVES; EFFICIENT; ACIDS;
D O I：
10.1002/slct.202004503
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A P(NMe2)(3)-mediated reductive (1+4) annulation reaction of alpha-keto esters with substituted nitroalkenes has been developed, providing a feasible protocol to construct polysubstituted isoxazoline N-oxides in moderate to excellent yields from readily available starting materials. This reaction originates from the characteristic reactivity of in situ generated Kukhtin-Ramirez adducts and presumably proceeds through a tandem Michael addition-intramolecular S(N)2 sequence. To further expand the utility of this annulation reaction, isoxazolines have been efficiently prepared from corresponding annulation products upon treatment with trimethyl phosphite.
引用
收藏
页码：4400 / 4403
页数：4
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