Stereospecific Synthesis of Fluorinated Pyrazolidinones and Isoxazolidines via a Catalyst-Free 1,3-Dipolar Cycloaddition of β-Fluoroalkylated α,β-Unsaturated 2-Pyridylsulfones

被引：10

作者：

Kou, Ying-Da ^{[1
]}

Zhao, Zhen-Ni ^{[1
]}

Yang, Xing ^{[1
]}

Kalita, Subarna Jyoti ^{[1
]}

Chen, Xue-Jian ^{[1
]}

Xie, Zhi-Zhong ^{[1
]}

Zhao, Yan ^{[2
]}

Huang, Yi-Yong ^{[1
]}

机构：

[1] Wuhan Univ Technol, Dept Chem, Sch Chem Chem Engn & Life Sci, 122 Luoshi Rd, Wuhan 430070, Hubei, Peoples R China

[2] Wuhan Univ Technol, Int Sch Mat Sci & Engn, State Key Lab Silicate Mat Architectures, 122 Luoshi Rd, Wuhan 430070, Hubei, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 09期

基金：

中国国家自然科学基金;

关键词：

cycloaddition; isoxazolidines; heterocyles; pyrazolidinones; stereoselectivity; AZOMETHINE IMINES; ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE SYNTHESIS; CHIRAL SULFONES; VINYL SULFONES; NITRONES; HETEROCYCLES; METHYLENEINDOLINONES; CONSTRUCTION; SULFONAMIDES;

D O I：

10.1002/ajoc.201800435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly atom-economic, regio- and stereospecific synthesis of fluorinated pyrazolidinones and isoxazolidines is disclosed under catalyst- and additive-free mild conditions. The diastereoselectivity with different type of 1,3-dipoles is elucidated by using DFT calculations in CH3CN. Furthermore, a reaction using a chiral azomethine imine, a gram-scale synthesis, and a reductive desulfonylation are also presented.

引用

页码：1830 / 1834

页数：5

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