[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

页码：4426 / 4431

页数：6

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