Regio- and Enantioselective Palladium-Catalyzed Asymmetric Allylation of N-Fluorenyl Trifluoromethyl Imine

被引：23

作者：

Wang, Wei ^{[1
,6
]}

Xiong, Qin ^{[2
,3
,4
,5
]}

Gong, Liang ^{[1
]}

Wang, Yingwei ^{[1
]}

Liu, Jie ^{[1
]}

Lan, Yu ^{[2
,3
,4
,5
]}

Zhang, Xia ^{[1
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy & Canc Ctr, Chengdu 610041, Peoples R China

[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China

[3] Zhengzhou Univ, Inst Green Catalysis, Zhengzhou 450001, Peoples R China

[4] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China

[5] Chongqing Univ, Chongqing Key Lab Theoret & Computat Chem, Chongqing 400030, Peoples R China

[6] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Coll Chem & Chem Engn, Nanchong 637009, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 14期

关键词：

ALPHA-AMINO-ACIDS; DECARBOXYLATIVE GENERATION; UMPOLUNG ALLYLATION; ALLYLIC ALKYLATION; EFFICIENT SYNTHESIS; AMINATIVE UMPOLUNG; 2-AZAALLYL ANIONS; VICINAL DIAMINES; ARYLATION; ACCESS;

D O I：

10.1021/acs.orglett.0c01836

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed asymmetric allylation of N-fluorenyl trifluoromethyl imine with allylic acetates is disclosed. This method provides scalable and efficient access to polysub-stituted chiral alpha-trifluoromethyl amines bearing two adjacent stereocenters and one allyl group in high yields with excellent regio-, diastereo-, and enantioselectivity. Importantly, this method also provides a powerful strategy for the synthesis of both regioisomeric products and the regioselectivity is controlled by the chiral catalysts and optically active substrates.

引用

页码：5479 / 5485

页数：7

共 82 条

[41] Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination [J].