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

[71] Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to ,-Disubstituted -Amino Acids [J].

Wei, Liang ;

Xu, Shi-Ming ;

Zhu, Qiao ;

Che, Chao ;

Wang, Chun-Jiang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (40) :12312-12316

[72] Chiral Aldehyde Catalysis for the Catalytic Asymmetric Activation of Glycine Esters [J].

Wen, Wei ;

Chen, Lei ;

Luo, Ming-Jing ;

Zhang, Yan ;

Chen, Ying-Chun ;

Ouyang, Qin ;

Guo, Qi-Xiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) :9774-9780

[73] Synthesis of Trifluoromethyl-Containing Vicinal Diamines by Asymmetric Decarboxylative Mannich Addition Reactions [J].

Wu, Lingmin ;

Xie, Chen ;

Mei, Haibo ;

Dai, Yanling ;

Han, Jianlin ;

Sooshonok, Vadim A. ;

Pan, Yi .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3187-3194

[74] Catalytic asymmetric umpolung reactions of imines [J].

Wu, Yongwei ;

Hu, Lin ;

Li, Zhe ;

Deng, Li .

NATURE, 2015, 523 (7561) :445-450

[75] Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives [J].

Xiao, Xiao ;

Xie, Ying ;

Su, Cunxiang ;

Liu, Mao ;

Shi, Yin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12914-12917

[76] Progress in asymmetric biomimetic transamination of carbonyl compounds [J].

Xie, Ying ;

Pan, Hongjie ;

Liu, Mao ;

Xiao, Xiao ;

Shi, Yian .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (07) :1740-1748

[77] Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction [J].

Xu, Shi-Ming ;

Wei, Liang ;

Shen, Chong ;

Xiao, Lu ;

Tao, Hai-Yan ;

Wang, Chun-Jiang .

NATURE COMMUNICATIONS, 2019, 10 (1)

[78] C-C bond-forming reactions via Pd-mediated decarboxylative α-imino anion generation [J].

Yeagley, Andrew A. ;

Chruma, Jason J. .

ORGANIC LETTERS, 2007, 9 (15) :2879-2882

[79] Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products [J].

Yus, Miguel ;

Gonzalez-Gomez, Jose C. ;

Foubelo, Francisco .

CHEMICAL REVIEWS, 2013, 113 (07) :5595-5698

[80] Intramolecular Umpolung Allylation of Imines [J].

Zhan, Miao ;

Pu, Xiang ;

He, Bin ;

Niu, Dawen ;

Zhang, Xia .

ORGANIC LETTERS, 2018, 20 (18) :5857-5860

← 1 2 3 4 5 6 7 8 9 →