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Synthesis 2023; 55(22): 3851-3861
DOI: 10.1055/a-2122-3731
paper

Direct Organocatalytic Asymmetric para C–H Aminoalkylation of Aniline Derivatives Affording Diarylmethylamines

Cheng-Long Wang‡
a   School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. of China
b   Affiliated Fengxian Hospital, Southern Medical University, Shanghai 201499, P. R. of China
,
Yong-Ling Li‡
a   School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, P. R. of China
,
Le Wang
c   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Xun-Hui Wang
c   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Jia Zhou
c   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
He-Yuan Bai
c   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Tong-Mei Ding∗
c   School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Zhen-Liang Sun∗
b   Affiliated Fengxian Hospital, Southern Medical University, Shanghai 201499, P. R. of China
› Author AffiliationsThis work was supported by the Innovation Fund (2019A005), the NSFC (22071147 and 81872418), Shanghai Scientific and Technological Innovation Action Plan (21S11902000), and the Transforming Medicine Cross Research Fund of Shanghai Jiao Tong University (YG2022QN032).
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Abstract

An efficient method to directly catalyze asymmetric para C–H aminoalkylation of aniline derivatives to prepare chiral diarylmethylamine system was developed. Aniline derivatives underwent an enantioselective aminoalkylation in the presence of chiral phosphoric acid, affording a series of optically active diarylmethylamine products in good yields and enantioselectivities (73% yield, 91% ee). Furthermore, this method could be used to prepare the key intermediate of chiral drug levocetirizine.

Key words

organic catalysis - aniline derivative - aminoalkylation - diarylmethylamine­ - asymmetric synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2122-3731.
  • Supporting Information


Publication History

Received: 09 May 2023

Accepted after revision: 03 July 2023

Accepted Manuscript online:
04 July 2023

Article published online:
16 August 2023

© 2023. Thieme. All rights reserved

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  • References

  • 1 Hu LA, Zhang Y, Zhang QW, Yin Q, Zhang X. Angew. Chem. Int. Ed. 2020; 59: 5321
    CrossrefPubMed
  • 2 Curran MP, Scott LJ, Perry CM. Drugs 2004; 64: 523
    CrossrefPubMed
  • 3 Mouridsen H, Gershanovich M, Sun Y, Pérez-Carrión R, Boni C, Monnier A, Apffelstaedt J, Smith R, Sleeboom HP, Jaenicke F, Pluzanska A, Dank M, Becquart D, Bapsy PP, Salminen E, Snyder R, Chaudri-Ross H, Lang R, Wyld P, Bhatnagar A. J. Clin. Oncol. 2003; 21: 2101
    CrossrefPubMed
    • 4a Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. J. Med. Chem. 2005; 48: 6597
      CrossrefPubMed
    • 4b Huang Y, Wang L, Li J, Qiu H, Leung P.-H. ACS Omega 2020; 5: 15936
      CrossrefPubMed
  • 5 Kim Y, Kwon YI, Kim S.-G. Synthesis 2019; 52: 281
    CrossrefPubMed
  • 6 Hermanns N, Dahmen S, Bolm C, Bräse S. Angew. Chem. Int. Ed. 2002; 41: 3692
    CrossrefPubMed
    • 7a Hayashi T, Ishigedani M. J. Am. Chem. Soc. 2000; 122: 976
      Crossref
    • 7b Oi S, Moro M, Kawanishi T, Inoue Y. Tetrahedron Lett. 2004; 45: 4855
      Crossref

      For selected examples of asymmetric synthesis of chiral diarylmethylamines through imine addition, see:
    • 8a Kuriyama M, Soeta T, Hao X, Chen Q, Tomioka K. J. Am. Chem. Soc. 2004; 126: 8128
      CrossrefPubMed
    • 8b Duan H.-F, Jia Y.-X, Wang L.-X, Zhou Q.-L. Org. Lett. 2006; 8: 2567
      CrossrefPubMed
    • 8c Jagt RB. C, Toullec PY, Geerdink D, de Vries JG, Feringa BL, Minnaard AJ. Angew. Chem. Int. Ed. 2006; 45: 2789
      CrossrefPubMed
    • 8d Shao C, Yu H.-J, Wu N.-Y, Feng C.-G, Lin G.-Q. Org. Lett. 2010; 12: 3820
      CrossrefPubMed
    • 8e Chen CC, Gopula B, Syu JF, Pan JH, Kuo TS, Wu PY, Henschke JP, Wu HL. J. Org. Chem. 2014; 79: 8077
      CrossrefPubMed
    • 8f Yasukawa T, Kuremoto T, Miyamura H, Kobayashi S. Org. Lett. 2016; 18: 2716
      CrossrefPubMed
    • 9a Tokunaga N, Otomaru Y, Okamoto K, Ueyama K, Shintani R, Hayashi T. J. Am. Chem. Soc. 2004; 126: 13584
      CrossrefPubMed
    • 9b Otomaru Y, Tokunaga N, Shintani R, Hayashi T. Org. Lett. 2005; 7: 307
      CrossrefPubMed
    • 9c Hao X, Kuriyama M, Chen Q, Yamamoto Y, Yamada K.-i, Tomioka K. Org. Lett. 2009; 11: 4470
      CrossrefPubMed
    • 9d Okamoto K, Hayashi T, Rawal VH. Chem. Commun. 2009; 4815
      CrossrefPubMed
    • 9e Jiang T, Chen WW, Xu MH. Org. Lett. 2017; 19: 2138
      CrossrefPubMed
    • 10a Ma G.-N, Zhang T, Shi M. Org. Lett. 2009; 11: 875
      CrossrefPubMed
    • 10b Dai H, Lu X. Tetrahedron Lett. 2009; 50: 3478
      Crossref
    • 10c Yang Z, Ni Y, Liu R, Song K, Lin S, Pan Q. Tetrahedron Lett. 2017; 58: 2034
      Crossref
    • 10d Song K, Wen M, Shen K, Fan C, Yang Z, Lin S, Pan Q. Tetrahedron Lett. 2021; 72: 153057
      CrossrefPubMed
    • 11a Nguyen TB, Bousserouel H, Wang Q, Guéritte F. Adv. Synth. Catal. 2011; 353: 257
      Crossref
    • 11b Kong D, Li M, Zi G, Hou G, He Y. J. Org. Chem. 2016; 81: 6640
      CrossrefPubMed
    • 11c Abdine RA. A, Hedouin G, Colobert F, Wencel-Delord J. ACS Catal. 2021; 11: 215
      Crossref

      For para C–H functionalization of aniline derivatives, see:
    • 12a Gathergood N, Zhuang W, Jørgensen KA. J. Am. Chem. Soc. 2000; 122: 12517
      Crossref
    • 12b Paras NA, MacMillan DW. C. J. Am. Chem. Soc. 2002; 124: 7894
      CrossrefPubMed
    • 12c Jia S, Xing D, Zhang D, Hu W. Angew. Chem. Int. Ed. 2014; 53: 13098
      CrossrefPubMed
    • 12d Xu B, Li M.-L, Zuo X.-D, Zhu S.-F, Zhou Q.-L. J. Am. Chem. Soc. 2015; 137: 8700
      CrossrefPubMed
    • 12e Chen J, Zou L, Zeng C, Zhou Y, Fan B. Org. Lett. 2018; 20: 1283
      CrossrefPubMed
    • 12f Zhou J, Zhu GD, Wang L, Tan FX, Jiang W, Ma ZG, Kang JC, Hou SH, Zhang SY. Org. Lett. 2019; 21: 8662
      CrossrefPubMed
    • 12g Liu C, Tan FX, Zhou J, Bai HY, Ding TM, Zhu GD, Zhang SY. Org. Lett. 2020; 22: 2173
      CrossrefPubMed
    • 13a Ram S, Spicer LD. Synth. Commun. 1987; 17: 415
      Crossref
    • 13b Doyle MP, Siegfried B, Dellaria JF. Jr. J. Org. Chem. 1977; 42: 2426
      Crossref
    • 13c O’Brien PA, Osborne S, Parker D. J. Chem. Soc., Perkin Trans. 1 1998; 2519
      Crossref
    • 14a Pflum DA, Krishnamurthy D, Han Z, Wald SA, Senanayake CH. Tetrahedron Lett. 2002; 43: 923
      Crossref
    • 14b Opalka CJ, Dambra TE, Faccone JJ, Bodson G, Cossement E. Synthesis 1995; 766
      Article in Thieme Connect