Synthesis of Chiral Diarylmethylamides via Catalytic Asymmetric Aza-Michael Addition of Amides to ortho-Quinomethanes

被引:0
作者
Qi, Suo-Suo [1 ]
Sun, Xiao-Ping [1 ]
Sun, Yan-Biao [1 ]
Zhai, Jing-Jing [1 ]
Wang, Yi-Feng [1 ]
Chu, Ming-Ming [2 ]
Xu, Dan-Qian [1 ]
机构
[1] Zhejiang Univ Technol, Catalyt Hydrogenat Res Ctr, State Key Lab Breeding Base Green Chem Synth Techn, Key Lab Green Pesticides & Cleaner Prod Technol Zh, Hangzhou 310014, Peoples R China
[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Peoples R China
关键词
ORTHO-QUINONE METHIDES; ENANTIOSELECTIVE SYNTHESIS; CARBOXYLIC-ACIDS; O-ALKYL; CYCLOADDITION; ANNULATION; ACCESS;
D O I
10.1021/acs.joc.3c01976
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral diarylmethylamides are a privileged skeleton in many bioactive molecules. However, the enantioselective synthesis of such molecules remains a long-standing challenge in organic synthesis. Herein, we report a chiral bifunctional squaramide catalyzed asymmetric aza-Michael addition of amides to in situ generated ortho-quinomethanes, affording enantioenriched diarylmethylamides in good yields with excellent enantioselectivities. This work not only provides a new strategy for the construction of the diarylmethylamides but also represents the practicability of amides as nitrogen-nucleophiles in asymmetric organocatalysis.
引用
收藏
页码:928 / 938
页数:11
相关论文
共 52 条
  • [41] Recent advances in the asymmetric synthesis of pharmacology-relevant nitrogen heterocycles via stereoselective aza-Michael reactions
    Vinogradov, Maxim G.
    Turova, Olga V.
    Zlotin, Sergei G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (15) : 3670 - 3708
  • [42] Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols
    Wang Haiqing
    Yang Shuang
    Zhang Yuchen
    Shi Feng
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 974 - 999
  • [43] Asymmetric Alkenyl C-H Functionalization by CpxRhIII forms 2H-Pyrrol-2-ones through [4+1]-Annulation of Acryl Amides and Allenes
    Wang, Shou-Guo
    Liu, Yang
    Cramer, Nicolai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (50) : 18136 - 18140
  • [44] Enantioselective Synthesis of Spiro Chroman-Isoindolinones via Formal (4+2) Cycloaddition of In Situ-Generated ortho-Quinone Methides with 3-Methylene Isoindolinones
    Wang, Tao
    Huang, Bo
    Wang, You-Qing
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (15) : 2596 - 2605
  • [45] Wang Z.-K., 2023, Angew. Chem., V135, DOI [10.1002/ange.202304706, DOI 10.1002/ANGE.202304706]
  • [46] Regioselective α-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins
    Wu, Bo
    Yu, Zhaoyuan
    Gao, Xiang
    Lan, Yu
    Zhou, Yong-Gui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 4006 - 4010
  • [47] Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes
    You, Yong
    Li, Ting-Ting
    Yuan, Shu-Pei
    Xie, Ke-Xin
    Wang, Zhen-Hua
    Zhao, Jian-Qiang
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (03) : 439 - 442
  • [48] Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes
    Zhang, Lanlan
    Geng, Yu
    Jin, Zhong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) : 3542 - 3552
  • [49] Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes
    Zhang, Tao
    Shen, Hong-Cheng
    Xu, Jia-Cheng
    Fan, Tao
    Han, Zhi-Yong
    Gong, Liu-Zhu
    [J]. ORGANIC LETTERS, 2019, 21 (07) : 2048 - 2051
  • [50] A New Type of Chiral Sulfinamide Monophosphine Ligands: Stereodivergent Synthesis and Application in Enantioselective Gold( I)Catalyzed Cycloaddition Reactions**
    Zhang, Zhan-Ming
    Chen, Peng
    Li, Wenbo
    Niu, Yanfei
    Zhao, Xiao-Li
    Zhang, Junliang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (17) : 4350 - 4354