手性双噁唑啉金属络合物催化N-α,β-不饱和酰基化合物与C,N-二芳基硝酮的不对称1,3-偶极环加成反应

doi:10.6023/cjoc201901004

有机化学 ›› 2019, Vol. 39 ›› Issue (6): 1642-1649.DOI: 10.6023/cjoc201901004 上一篇下一篇

所属专题：金属有机化学

研究论文

手性双噁唑啉金属络合物催化N-α,β-不饱和酰基化合物与C,N-二芳基硝酮的不对称1,3-偶极环加成反应

李明龙, 曹茜娴, 由君, 喻艳超, 武文菊, 刘波

哈尔滨理工大学化学与环境工程学院绿色化工技术黑龙江省高校重点实验室哈尔滨 150040

收稿日期:2019-01-04 修回日期:2019-03-02 发布日期:2019-05-15
通讯作者: 由君, 喻艳超 E-mail:youjunjun@126.com;yycyychao@163.com
基金资助:
黑龙江省自然科学基金（No.LH2019B010）、国家自然科学基金（No.21506043）资助项目.

Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex

Li Minglong, Cao Xixian, You Jun, Yu Yanchao, Wu Wenju, Liu Bo

Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040

Received:2019-01-04 Revised:2019-03-02 Published:2019-05-15
Contact: 10.6023/cjoc201901004 E-mail:youjunjun@126.com;yycyychao@163.com
Supported by:
Project supported by the Natural Science Foundation of Heilongjiang Province (No. LH2019B010), and the National Natural Science Foundation of China (No. 21506043).

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1. 手性双噁唑啉金属络合物催化N-α,β-不饱和酰基化合物与C,N-二芳基硝酮的不对称1,3-偶极环加成反应.PDF(2076KB)

摘要/Abstract

研究了Inda-BOX 1金属络合物为催化剂的两种缺电子烯烃与C，N-二芳基硝酮的不对称环加成反应.研究结果表明，在催化剂存在的条件下，两反应均可得到4-位取代产物.其中N-丙烯酰基噁唑烷酮为亲偶极体时，反应的exo/endo选择性达到100/0，且exo产物的ee值高达97%；N-丙烯酰基-3，5-二甲基吡唑为亲偶极体时，exo/endo选择性为0/100，且endo产物的ee值高达98%.对亲偶极体及硝酮结构与反应选择性之间的关系进行了初步探讨.

关键词: 不对称催化, 1,3-偶极环加成反应, 手性双噁唑啉, N-α,β-不饱和酰基化合物, C,N-二芳基硝酮, 对映体选择性

Asymmetric cycloaddition reactions catalyzed by Inda-BOX 1 metal complex between two kinds of electron-withdrawing alkenes and C,N-diarylnitrone have been studied respectively. Results showed that the 4-substituted products were mainly obtained in both reactions under the best conditions. When N-acryloyl oxazolidinone was used as dipolarophile, the exo/endo selectivity of the reaction was 100/0, and the ee of the exo product was as high as 97%. When N-acryloyl-3,5-dimethyl pyrazole was used as dipolarophile, the selectivity of exo/endo was 0/100, and the ee of endo product was up to 98%. The relationship of the dipolarophile, the structure of nitrone and the selectivity of the reaction was discussed.

Key words: asymmetric catalysis, 1,3-dipolar cycloaddition reaction, chiral dioxazoline, N-α,β-unsaturated acyl compounds, C,N-diarylnitrone, enantioselectivity

引用此文

李明龙, 曹茜娴, 由君, 喻艳超, 武文菊, 刘波. 手性双噁唑啉金属络合物催化N-α,β-不饱和酰基化合物与C,N-二芳基硝酮的不对称1,3-偶极环加成反应[J]. 有机化学, 2019, 39(6): 1642-1649.

Li Minglong, Cao Xixian, You Jun, Yu Yanchao, Wu Wenju, Liu Bo. Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex[J]. Chin. J. Org. Chem., 2019, 39(6): 1642-1649.

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手性双噁唑啉金属络合物催化N-α,β-不饱和酰基化合物与C,N-二芳基硝酮的不对称1,3-偶极环加成反应

Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex

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