[4+2] Cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3

被引：4
|
作者：
Fu, Yiwei [1 ,2 ]
Qin, Cong [1 ,2 ]
Zhang, Zhiqiang [3 ,4 ,5 ]
Shi, Haoyu [1 ,2 ]
Zhao, Jianbo [1 ,2 ]
Gong, Xueqing [3 ,4 ,5 ]
Shi, Lei [6 ]
Li, Hao [1 ,2 ]
机构：
[1] East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
[4] East China Univ Sci & Technol, Sch Chem & Mol Engn, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Ctr C, 130 Meilong Rd, Shanghai 200237, Peoples R China
[5] East China Univ Sci & Technol, Sch Chem & Mol Engn, Res Inst Ind Catalysis, 130 Meilong Rd, Shanghai 200237, Peoples R China
[6] Huabao Flavours & Fragrances Co Ltd, 1299 Yecheng Rd, Shanghai 201822, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 16期
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; FLUORINE ELIMINATION; GEM-DIFLUOROALKENES; UMPOLUNG REACTIONS; ACTIVATION; FUNCTIONALIZATION; EFFICIENT; ACCESS; MONO; DERIVATIVES;
D O I：
10.1039/d1qo00639h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a new [4 + 2] cycloaddition of trifluoromethyl ketimines with 2-alkenyl azaarenes through selective C-F bond cleavage of CF3. The reactions are promoted by 2,2,6,6-tetramethylpiperidine (TMP) under mild conditions to give cis-tetrahydropyridine products in moderate yields. Density functional theory (DFT) calculations reveal that the in situ formed (E)-N-(2,2-difluoro-1-phenylvinyl)-1-phenylmethanimine is the key intermediate for the formation of cis-tetrahydropyridine products which have the lowest energy among the four possible products.
引用
收藏
页码：4426 / 4431
页数：6
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