PDF herunterladen
Synthesis 2022; 54(02): 421-428
DOI: 10.1055/a-1643-8526
paper

Enantioselective Transfer Hydrogenation of Oxocarbenium Ions Enables Asymmetric Access to α-Substituted 1,3-Dihydroisobenzofurans

Likai Zhou
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
Kuiyong Jia
b   Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan 250012, P. R. of China
,
Xigong Liu∗
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
,
Lei Liu  ∗
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
› InstitutsangabenThis work was financially supported by the Postdoctoral Innovation Project of Shandong Province (No. 202001003), the National Science Foundation of China (No. 21801093), and China Postdoctoral Science Foundation (No. 2019M662321).
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

Reported here is an efficient enantioselective transfer hydrogenation of cyclic oxocarbenium ions generated in situ through collapse of the corresponding acetal substrates. The asymmetric approach provides straightforward access to a variety of chiral α-aryl substituted 1,3-dihydroisobenzofurans in high yields with excellent enantioselectivities. α-Alkynyl substituted 1,3-dihydroisobenzofurans were also proved to be suitable substrates. In addition, when the reaction was performed at gram scale, the desired product was obtained in good yields with excellent enantioselectivity.

Key words

enantioselectivity - transfer hydrogenation - oxocarbenium ions - α-substituted 1,3-dihydroisobenzofurans - asymmetric catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1643-8526.
  • Supporting Information


Publikationsverlauf

Eingereicht: 22. Juli 2021

Angenommen nach Revision: 17. August 2021

Accepted Manuscript online:
13. September 2021

Artikel online veröffentlicht:
17. September 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Harper JK, Arif AM, Ford EJ, Strobel GA, Porco JA. Jr, Tomer DP, Oneill KL, Heider EM, Grant DM. Tetrahedron 2003; 59: 2471
      CrossrefPubMed
    • 1b Sindrup SH, Bjerre U, Dejgaard A, Brøsen K, Aaes-Jørgensen T, Gram LF. Clin. Pharmacol. Ther. 1992; 52: 547
      CrossrefPubMed
    • 1c Keller MB. J. Clin. Psychiatry 2000; 61: 896
      CrossrefPubMed
    • 1d Vedantham R, Vetukuri PR, Boini A, Khagga M, Bandichhor R. Org. Process Res. Dev. 2013; 17: 798
      Crossref
    • 1e Hewitt JF. M, Williams L, Aggarwal P, Smith CD, France DJ. Chem. Sci. 2013; 4: 3538
      Crossref
    • 1f Bueno AB, Gilmore J, Boot J, Broadmore R, Cooper J, Findlay J, Hayhurst L, Marcos A, Montero C, Mitchell S, Timms G, Tomlinson R, Wallace L, Walton L. Bioorg. Med. Chem. Lett. 2007; 17: 3344
      CrossrefPubMed
    • 2a Gabriele B, Salerno G, Fazio A, Pittelli R. Tetrahedron 2003; 59: 6251
      Crossref
    • 2b Della Ca’ N, Campanini F, Gabriele B, Salerno G, Massera C, Costa M. Adv. Synth. Catal. 2009; 351: 2423
      Crossref
    • 2c Mancuso R, Mehta S, Gabriele B, Salerno G, Jenks WS, Larock RC. J. Org. Chem. 2010; 75: 897
      CrossrefPubMed
    • 2d Sekine K, Takayanagi A, Kikuchi S, Yamada T. Chem. Commun. 2013; 49: 11320
      CrossrefPubMed
    • 2e Shen H, Fu J, Gong J, Yang Z. Org. Lett. 2014; 16: 5588
      CrossrefPubMed
    • 2f Zhang W.-Z, Yang M.-W, Yang X.-T, Shi L.-L, Wang H.-B, Lu X.-B. Org. Chem. Front. 2016; 3: 217
      Crossref
    • 2g Liu S, Chen K, Hao W.-J, Tu X.-C, Tu S.-J, Jiang B. J. Org. Chem. 2019; 84: 1964
      CrossrefPubMed
    • 3a Čorić I, Kim JH, Vlaar T, Patil M, Thiel W, List B. Angew. Chem. Int. Ed. 2013; 52: 3490
      CrossrefPubMed
    • 3b Ravindra B, Das BG, Ghorai P. Org. Lett. 2014; 16: 5580
      CrossrefPubMed
    • 3c Chen D, Chemler SR. Org. Lett. 2018; 20: 6453
      CrossrefPubMed
    • 3d Chen D, Berhane IA, Chemler SR. Org. Lett. 2020; 22: 7409
      CrossrefPubMed
  • 4 Weldy NM, Schafer AG, Owens CP, Herting CJ, Varela-Alvarez A, Chen S, Niemeyer Z, Musaev DG, Sigman MS, Davies HM. L, Blakey SB. Chem. Sci. 2016; 7: 3142
    CrossrefPubMed
    • 5a Sun S, Ma Y, Liu Z, Liu L. Angew. Chem. Int. Ed. 2021; 60: 176
      CrossrefPubMed
    • 5b Sun S, Yang Y, Zhao R, Zhang D, Liu L. J. Am. Chem. Soc. 2020; 142: 19346
      CrossrefPubMed
    • 6a Kuznetsov E.-V, Shcherbakova I.-V, Balaban A.-T. Adv. Heterocycl. Chem. 1990; 50: 157
      Crossref
    • 6b Asao N, Takahashi K, Lee S, Kasahara T, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 12650
      CrossrefPubMed
    • 6c Asao N, Takahashi K, Yamamoto Y. Angew. Chem. Int. Ed. 2003; 42: 3504
      CrossrefPubMed
    • 6d Zhu J, Germain AR, Porco JA. Jr. Angew. Chem. Int. Ed. 2004; 43: 1239
      CrossrefPubMed
    • 6e Kusama H, Funami H, Shido M, Hara Y, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2005; 127: 2709
      CrossrefPubMed
    • 6f Hsu Y.-C, Ting C.-M, Liu R.-S. J. Am. Chem. Soc. 2009; 131: 2090
      CrossrefPubMed
    • 6g Hu Z.-L, Yang Z.-Y, Wang S, Yao Z.-J. Chem. Eur. J. 2011; 17: 1268
      CrossrefPubMed
    • 6h Guo B, Zhou Y, Zhang L, Hua R. J. Org. Chem. 2015; 80: 7635
      CrossrefPubMed
    • 6i Meng Z, Sun S, Yuan H, Lou H, Liu L. Angew. Chem. Int. Ed. 2014; 53: 543
      CrossrefPubMed
  • 7 Reisman SE, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 7198
    • 9a Dasgupta S, Rivas T, Watson MP. Angew. Chem. Int. Ed. 2015; 54: 14154
      CrossrefPubMed
    • 9b Haidzinskaya T, Kerchner HA, Liu J, Watson MP. Org. Lett. 2015; 17: 3857
      CrossrefPubMed
    • 9c Maity P, Srinivas HD, Watson MP. J. Am. Chem. Soc. 2011; 133: 17142
      CrossrefPubMed
    • 10a Saito K, Kajiwara Y, Akiyama T. Angew. Chem. Int. Ed. 2013; 52: 13284
      CrossrefPubMed
    • 10b Terada M, Li F, Toda Y. Angew. Chem. Int. Ed. 2014; 53: 235
      CrossrefPubMed
    • 10c Hsiao C.-C, Liao H.-H, Sugiono E, Atodiresei I, Rueping M. Chem. Eur. J. 2013; 19: 9775
      CrossrefPubMed
    • 10d Wan M, Sun S, Li Y, Liu L. Angew. Chem. Int. Ed. 2017; 56: 5116
      CrossrefPubMed
    • 10e Miao T, Tian Z.-Y, He Y.-M, Chen F, Chen Y, Yu Z.-X, Fan Q.-H. Angew. Chem. Int. Ed. 2017; 56: 4135
      CrossrefPubMed
    • 10f Yang T, Sun Y, Wang H, Lin Z, Wen J, Zhang X. Angew. Chem. Int. Ed. 2020; 59: 6108
      CrossrefPubMed
    • 11a Chen J.-R, Hu X.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2014; 53: 4038
      CrossrefPubMed
    • 11b Hojo D, Noguchi K, Tanaka K. Angew. Chem. Int. Ed. 2009; 48: 8129
      CrossrefPubMed
    • 11c Ishida K, Kusama H, Iwasawa N. J. Am. Chem. Soc. 2010; 132: 8842
      CrossrefPubMed
    • 11d Handa S, Slaughter LM. Angew. Chem. Int. Ed. 2012; 51: 2912
      CrossrefPubMed
    • 11e Yu S.-Y, Zhang H, Gao Y, Mo L, Wang S, Yao Z.-J. J. Am. Chem. Soc. 2013; 135: 11402
      CrossrefPubMed
    • 11f Terada M, Toda Y. Angew. Chem. Int. Ed. 2012; 51: 2093
      CrossrefPubMed
    • 11g Qian H, Zhao W.-X, Wang Z.-B, Sun J.-W. J. Am. Chem. Soc. 2015; 137: 560
      CrossrefPubMed
    • 12a Lee S, Kaib PS. J, List B. J. Am. Chem. Soc. 2017; 139: 2156
      CrossrefPubMed
    • 12b Zhao C, Chen SB, Seidel D. J. Am. Chem. Soc. 2016; 138: 9053
      CrossrefPubMed
  • 13 Chen X, Zhao R, Liu Z, Sun S, Ma Y, Liu Q, Sun X, Liu L. Chin. Chem. Lett. 2021; 32: 2305
    Crossref