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
相关论文
共 82 条
  • [41] Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination
    Liu, Yong Ethan
    Lu, Zhaole
    Li, Bo
    Tian, Jiaxin
    Liu, Feng
    Zhao, Junyu
    Hou, Chengkang
    Li, Yingkun
    Niu, Lili
    Zhao, Baoguo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10730 - 10733
  • [42] Loiseleur O, 2000, HELV CHIM ACTA, V83, P2287, DOI 10.1002/1522-2675(20000906)83:9<2287::AID-HLCA2287>3.0.CO
  • [43] 2-J
  • [44] Catalytic imine-imine cross-coupling reactions
    Matsumoto, Masatoshi
    Harada, Masashi
    Yamashita, Yasuhiro
    Kobayashi, Shu
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (86) : 13041 - 13044
  • [45] Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates
    Nie, Jing
    Guo, Hong-Chao
    Cahard, Dominique
    Ma, Jun-An
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 455 - 529
  • [46] Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes
    Onyeagusi, Chibueze, I
    Shao, Xinxin
    Malcolmson, Steven
    [J]. ORGANIC LETTERS, 2020, 22 (04) : 1681 - 1685
  • [47] Palladium-Catalyzed Decarboxylative Generation and Asymmetric Allylation of α-Imino Anions
    Qian, Xiaoyan
    Ji, Pengfei
    He, Chang
    Zirimwabagabo, Jean-Olivier
    Archibald, Michelle M.
    Yeagley, Andrew A.
    Chruma, Jason J.
    [J]. ORGANIC LETTERS, 2014, 16 (19) : 5228 - 5231
  • [48] Synthesis and Applications of tert-Butanesulfinamide
    Robak, MaryAnn T.
    Herbage, Melissa A.
    Ellman, Jonathan A.
    [J]. CHEMICAL REVIEWS, 2010, 110 (06) : 3600 - 3740
  • [49] METHODS OF REACTIVITY UMPOLUNG
    SEEBACH, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04): : 239 - 258
  • [50] Catalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines
    Shen, Chong
    Wang, Ruo-Qing
    Wei, Liang
    Wang, Zuo-Fei
    Tao, Hai-Yan
    Wang, Chun-Jiang
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6940 - 6945