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Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters

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† State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 73000, China
‡ University of Chinese Academy of Sciences, Beijing 100049, China
*E-mail: [email protected]
Cite this: Org. Lett. 2017, 19, 13, 3676–3679
Publication Date (Web):June 21, 2017
https://doi.org/10.1021/acs.orglett.7b01740
Copyright © 2017 American Chemical Society
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Abstract

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A copper-catalyzed asymmetric protoboration of both Z-β-amidoacrylonitriles and ethyl E-β-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral α-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral α-amino boronate esters.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b01740.

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Cited By

This article is cited by 25 publications.

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  2. Jian-Fei Wang, Xin Meng, Chao-Huan Zhang, Chuan-Ming Yu, Bin Mao. Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives. Organic Letters 2020, 22 (19) , 7427-7432. https://doi.org/10.1021/acs.orglett.0c02394
  3. Dongyang Fan, Jian Zhang, Yanhua Hu, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang. Asymmetric Hydrogenation of α-Boryl Enamides Enabled by Nonbonding Interactions. ACS Catalysis 2020, 10 (5) , 3232-3240. https://doi.org/10.1021/acscatal.9b04543
  4. Wenbo Ming, Xiaocui Liu, Alexandra Friedrich, Johannes Krebs, Todd B. Marder. The Borono–Strecker Reaction: Synthesis of α-Aminoboronates via a Multicomponent Reaction of Carbonyl Compounds, Amines, and B2pin2. Organic Letters 2020, 22 (2) , 365-370. https://doi.org/10.1021/acs.orglett.9b03773
  5. Xiao-Yan Bai, Wei Zhao, Xin Sun, Bi-Jie Li. Rhodium-Catalyzed Regiodivergent and Enantioselective Hydroboration of Enamides. Journal of the American Chemical Society 2019, 141 (50) , 19870-19878. https://doi.org/10.1021/jacs.9b10578
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  7. C. Benjamin Schwamb, Keegan P. Fitzpatrick, Alexander C. Brueckner, H. Camille Richardson, Paul H.-Y. Cheong, Karl A. Scheidt. Enantioselective Synthesis of α-Amidoboronates Catalyzed by Planar-Chiral NHC-Cu(I) Complexes. Journal of the American Chemical Society 2018, 140 (34) , 10644-10648. https://doi.org/10.1021/jacs.8b05045
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  9. Sherif J. Kaldas, Tatiana Rogova, Valentine G. Nenajdenko, Andrei K. Yudin. Modular Synthesis of β-Amino Boronate Peptidomimetics. The Journal of Organic Chemistry 2018, 83 (13) , 7296-7302. https://doi.org/10.1021/acs.joc.8b00325
  10. Xu-Cheng Gan, Qi Zhang, Xue-Shun Jia, and Liang Yin . Asymmetric Construction of Fluoroalkyl Tertiary Alcohols through a Three-Component Reaction of (Bpin)2, 1,3-Enynes, and Fluoroalkyl Ketones Catalyzed by a Copper(I) Complex. Organic Letters 2018, 20 (4) , 1070-1073. https://doi.org/10.1021/acs.orglett.7b04039
  11. Aurora López, Timothy B. Clark, Alejandro Parra, and Mariola Tortosa . Copper-Catalyzed Enantioselective Synthesis of β-Boron β-Amino Esters. Organic Letters 2017, 19 (23) , 6272-6275. https://doi.org/10.1021/acs.orglett.7b02784
  12. Fu‐Peng Wu, Xiao‐Feng Wu. Ligand‐Controlled Copper‐Catalyzed Regiodivergent Carbonylative Synthesis of α‐Amino Ketones and α‐Boryl Amides from Imines and Alkyl Iodides. Angewandte Chemie 2021, 133 (2) , 705-710. https://doi.org/10.1002/ange.202012251
  13. Fu‐Peng Wu, Xiao‐Feng Wu. Ligand‐Controlled Copper‐Catalyzed Regiodivergent Carbonylative Synthesis of α‐Amino Ketones and α‐Boryl Amides from Imines and Alkyl Iodides. Angewandte Chemie International Edition 2021, 60 (2) , 695-700. https://doi.org/10.1002/anie.202012251
  14. Yang Xi, Chenchen Wang, Qian Zhang, Jingping Qu, Yifeng Chen. Palladium‐Catalyzed Regio‐, Diastereo‐, and Enantioselective 1,2‐Arylfluorination of Internal Enamides. Angewandte Chemie International Edition 2020, 132 https://doi.org/10.1002/anie.202012882
  15. Yang Xi, Chenchen Wang, Qian Zhang, Jingping Qu, Yifeng Chen. Palladium‐Catalyzed Regio‐, Diastereo‐, and Enantioselective 1,2‐Arylfluorination of Internal Enamides. Angewandte Chemie 2020, 132 https://doi.org/10.1002/ange.202012882
  16. Jimil George, Hun Young Kim, Kyungsoo Oh. Copper( i )/DM-SEGPHOS-catalyzed enantio- and diastereoselective conjugate boration to α-alkylidene-γ-lactams. Organic Chemistry Frontiers 2020, 7 (4) , 709-714. https://doi.org/10.1039/C9QO01504C
  17. Yazhou Lou, Jun Wang, Gelin Gong, Fanfu Guan, Jiaxiang Lu, Jialin Wen, Xumu Zhang. Catalytic asymmetric hydrogenation of ( Z )-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters. Chemical Science 2020, 11 (3) , 851-855. https://doi.org/10.1039/C9SC04534A
  18. Alejandro Parra, Laura Trulli, Mariola Tortosa. Copper‐Catalyzed Addition of Diboron Species. 2020,,, 1-82. https://doi.org/10.1002/9780470682531.pat0976
  19. Andrej Šterman, Izidor Sosič, Stanislav Gobec, Zdenko Časar. Synthesis of aminoboronic acid derivatives: an update on recent advances. Organic Chemistry Frontiers 2019, 6 (16) , 2991-2998. https://doi.org/10.1039/C9QO00626E
  20. Suman Chakrabarty, Hector Palencia, Martha D. Morton, Ryan O. Carr, James M. Takacs. Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration. Chemical Science 2019, 10 (18) , 4854-4861. https://doi.org/10.1039/C8SC05613G
  21. Stephen N. Hyland, Ellie A. Meck, Mariola Tortosa, Timothy B. Clark. α-Amidoboronate esters by amide-directed alkane C H borylation. Tetrahedron Letters 2019, 60 (16) , 1096-1098. https://doi.org/10.1016/j.tetlet.2019.03.020
  22. Yajuan Zhang, Min Tong, Qian Gao, Panke Zhang, Senmiao Xu. NHC-copper-catalyzed asymmetric conjugate silylation of access chiral α-aminosilanes. Tetrahedron Letters 2019, 60 (17) , 1210-1212. https://doi.org/10.1016/j.tetlet.2019.03.072
  23. Qingqing Qi, Xuena Yang, Xiaoping Fu, Shiqing Xu, Ei‐ichi Negishi. Highly Enantiospecific Borylation for Chiral α‐Amino Tertiary Boronic Esters. Angewandte Chemie 2018, 130 (46) , 15358-15362. https://doi.org/10.1002/ange.201809389
  24. Qingqing Qi, Xuena Yang, Xiaoping Fu, Shiqing Xu, Ei‐ichi Negishi. Highly Enantiospecific Borylation for Chiral α‐Amino Tertiary Boronic Esters. Angewandte Chemie International Edition 2018, 57 (46) , 15138-15142. https://doi.org/10.1002/anie.201809389
  25. Lili Chen, Jun-Jian Shen, Qian Gao, Senmiao Xu. Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles. Chemical Science 2018, 9 (26) , 5855-5859. https://doi.org/10.1039/C8SC01815D

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