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

被引:21
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
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
收藏
页码:5479 / 5485
页数:7
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