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Synlett 2023; 34(04): 301-313
DOI: 10.1055/a-1986-7969
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Special Edition Thieme Chemistry Journals Awardees 2022

Asymmetric Formal [3+2] Cycloaddition Reactions of 3-Isothio­cyanato Oxindoles: an Update

Fen Tan‡
a   Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients, School of Chemistry and Life Sciences, Hubei University of Education, Wuhan, Hubei 430205, P. R. of China
,
Xiao-Yu He‡
b   College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, 8 Daxue Road, Yichang, Hubei 443002, P. R. of China
c   School of Pharmaceutical Sciences, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, Wuhan University, Wuhan 430071, P. R. of China
,
Qing-Qing Yang∗
b   College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, 8 Daxue Road, Yichang, Hubei 443002, P. R. of China
,
You-Quan Zou∗
c   School of Pharmaceutical Sciences, Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, Wuhan University, Wuhan 430071, P. R. of China
d   TaiKang Center for Life and Medical Sciences, Wuhan University, Wuhan 430071, P. R. of China
› Author AffiliationsThis work was supported by the Natural Science Foundation of Hubei Province (No. 2022CFB413), the National Natural Science Foundation of China (Nos. 21602052 and 21702121), the 111 Project (D20015), the start-up funding from Wuhan University (Nos. 691000002 and 600460026) and the TaiKang Center for Life and Medical Sciences, Wuhan University (No. 692000007).
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Abstract

3-Isothiocyanato oxindoles are a class of important building blocks which have been widely used in the synthesis of structurally diverse enantioenriched spirooxindoles. In this short review, it is attempted to cover the recent synthetic aspects of 3-isothiocyanato oxindoles participated cascade cyclizations in the last few years (i.e., from 2017 to 2022), with an emphasis on formal [3+2] cycloaddition reactions.

1 Introduction

2 Organocatalyzed Formal [3+2] Cycloaddition of 3-Isothiocyanato Oxindoles

3 Lewis Acid Catalyzed Formal [3+2] Cycloaddition of 3-Isothiocyanato Oxindoles

4 Conclusions

Key words

spirooxindoles - 3-isothiocyanato oxindoles - asymmetric synthesis - organocatalysis - Lewis acid catalysis - cycloaddition reaction


Publication History

Received: 16 November 2022

Accepted after revision: 24 November 2022

Accepted Manuscript online:
24 November 2022

Article published online:
21 December 2022

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  • References


      • For selected reviews, see:
    • 2a Lin H, Danishefsky SJ. Angew. Chem. Int. Ed. 2003; 42: 36
      CrossrefPubMed
    • 2b Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
      Crossref
    • 2c Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
      CrossrefPubMed
    • 2d Ye N, Chen H.-Y, Wold EA, Shi P.-Y, Zhou J. ACS Infect. Dis. 2016; 2: 382
      CrossrefPubMed
    • 2e Wan Y, Li Y, Yan C, Yan M, Tang Z. Eur. J. Med. Chem. 2019; 183: 111691
      CrossrefPubMed

      For selected examples, see:
    • 3a Vine KL, Matesic L, Locke JM, Ranson M, Skropeta D. Anti-Cancer Agents Med. Chem. 2009; 9: 397
      CrossrefPubMed
    • 3b Rottmann M, McNamara C, Yeung BK, Lee MC, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, Gonzalez-Paez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck HP, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
      CrossrefPubMed
    • 3c Badillo JJ, Hanhan NV, Franz AK. Curr. Opin. Drug Discovery Dev. 2010; 13: 758
    • 3d Arun Y, Bhaskar G, Balachandran C, Ignacimuthu S, Perumal PT. Bioorg. Med. Chem. Lett. 2013; 23: 1839
      CrossrefPubMed
    • 3e Das D, Banerjee R, Mitra A. J. Chem. Pharm. Res. 2014; 6: 108
    • 3f Bian Z, Marvin CC, Petersson M, Martin SF. J. Am. Chem. Soc. 2014; 136: 14184
      CrossrefPubMed
    • 3g Kathirvelan D, Haribabu J, Reddy BS. R, Balachandran C, Duraipandiyan V. Bioorg. Med. Chem. Lett. 2015; 25: 389
      CrossrefPubMed

      For selected reviews, see:
    • 4a Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
      Crossref
    • 4b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
      CrossrefPubMed
    • 4c Cao Z.-Y, Zhou F, Zhou J. Acc. Chem. Res. 2018; 51: 1443
      CrossrefPubMed
    • 4d Cheng D, Ishihara Y, Tan B, Barbas CF. ACS Catal. 2014; 4: 743
      CrossrefPubMed
    • 4e Gasperi T, Miceli M, Campagne J.-M, de Figueiredo RM. Molecules 2017; 22: 1636
      CrossrefPubMed
    • 4f Mei G.-J, Shi F. Chem. Commun. 2018; 54: 6607
      CrossrefPubMed
    • 4g Gui H.-Z, Wei Y, Shi M. Chem. Asian J. 2020; 15: 1225
      CrossrefPubMed
    • 4h Lin Y, Du D.-M. Chin. J. Org. Chem. 2020; 40: 3214
      Crossref
    • 4i Laviós A, Sanz-Marco A, Vila C, Blay G, Pedro JR. Eur. J. Org. Chem. 2021; 2268
      Crossref
  • 5 Chen W.-B, Wu Z.-J, Hu J, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2011; 13: 2472
    CrossrefPubMed

      • For reviews, see:
    • 6a Han W.-Y, Zhao J.-Q, Zuo J, Xu X.-Y, Zhang X.-M, Yuan W.-C. Adv. Synth. Catal. 2015; 357: 3007
      Crossref
    • 6b Tan F, Xiao W.-J, Zeng G.-P. Chin. J. Org. Chem. 2017; 37: 824
      Crossref
  • 7 Wang L.-Q, Yang D.-X, Li D, Wang R. Org. Lett. 2015; 17: 3004
    CrossrefPubMed
    • 8a Tietze LF, Brasche G, Gericke KM. Domino Reaction in Organic Synthesis . Wiley-VCH; Weinheim: 2006
      CrossrefGoogle Scholar
    • 8b Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
      CrossrefPubMed
    • 8c Volla CM, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390
      CrossrefPubMed
    • 8d Du D, Xu Q, Li X.-G, Shi M. Chem. Eur. J. 2016; 22: 4733
      CrossrefPubMed

      For selected reviews, see:
    • 9a Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
      Crossref
    • 9b Gasperi T, Vetica F, de Figueiredo R, Orsini M, Tofani D. Synthesis 2015; 47: 2139
      Article in Thieme Connect
    • 9c Tian L, Luo Y.-C, Hu X.-Q, Xu P.-F. Asian J. Org. Chem. 2016; 5: 580
      Crossref
    • 9d Chanda T, Zhao JC.-G. Adv. Synth. Catal. 2018; 360: 2
      Crossref
    • 10a Malerich JP, Hagihara K, Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416
      CrossrefPubMed
    • 10b Storer RI, Aciro C, Jones LH. Chem. Soc. Rev. 2011; 40: 2330
      CrossrefPubMed
    • 10c Rouf A, Tanyeli C. Curr. Org. Chem. 2016; 20: 2996
      Crossref
    • 10d Han X, Zhou H.-B, Dong C. Chem. Rec. 2016; 16: 897
      CrossrefPubMed
  • 11 Lin Y, Liu L, Du D.-M. Org. Chem. Front. 2017; 4: 1229
    CrossrefPubMed
  • 12 Song Y.-X, Du D.-M. Synthesis 2018; 50: 1535
    Article in Thieme Connect
  • 13 Lin N, Long X.-W, Chen Q, Zhu W.-R, Wang B.-C, Chen K.-B, Jiang C.-W, Weng J, Lu G. Tetrahedron 2018; 74: 3734
    CrossrefPubMed
  • 14 Liu XL, Gong Y, Chen S, Zuo X, Yao Z, Zhou Y. Org. Chem. Front. 2019; 6: 1603
    Crossref
  • 15 Chen S, Wang G.-L, Xu S.-W, Tian M.-Y, Zhang M, Liu X.-L, Yuan W.-C. Org. Biomol. Chem. 2019; 17: 6551
    CrossrefPubMed
  • 16 Zhang L.-L, Da B.-C, Xiang S.-H, Zhu S, Yuan Z.-Y, Guo Z, Tan B. Tetrahedron 2019; 75: 1689
    CrossrefPubMed
  • 17 Bai M, Chen Y.-Z, Cui B.-D, Xu X.-Y, Yuan W.-C. Tetrahedron 2019; 75: 2155
    CrossrefPubMed
    • 18a Murugan R, Anbazhagan S, Sriman Narayanan S. Eur. J. Med. Chem. 2009; 44: 3272
      CrossrefPubMed
    • 18b Ranjith Kumar R, Perumal S, Senthilkumar P, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2009; 44: 3821
      CrossrefPubMed
    • 18c Karthikeyan K, Sivakumar PM, Doble M, Perumal PT. Eur. J. Med. Chem. 2010; 45: 3446
      CrossrefPubMed
  • 19 Gui H.-Z, Meng Z, Xiao Z.-S, Yang Z.-R, Wei Y, Shi M. Eur. J. Org. Chem. 2020; 6614
    CrossrefPubMed
    • 20a Klásek A, Mrkvička V, Lyčka A, Mikšík I, Růžička A. Tetrahedron 2009; 65: 4908
      Crossref
    • 20b Zhao BL, Du DM. Org. Lett. 2018; 20: 3797
      CrossrefPubMed
  • 21 Gui H.-Z, Wei Y, Shi M. Org. Biomol. Chem. 2018; 16: 9218
    CrossrefPubMed
  • 22 Zhang C.-B, Dou P.-H, You Y, Wang Z.-H, Zhou M.-Q, Xu X.-Y, Yuan W.-C. Tetrahedron 2019; 75: 130571
    CrossrefPubMed
  • 23 Zhang C.-B, Dou P.-H, Zhao J.-Q, Yuan W.-C. Tetrahedron 2020; 76: 131116
    CrossrefPubMed

      • For selected reviews, see:
    • 24a Zheng C, You S.-L. Nat. Prod. Rep. 2019; 36: 1589
      CrossrefPubMed
    • 24b Xia Z.-L, Xu-Xu Q.-F, Zheng C, You S.-L. Chem. Soc. Rev. 2020; 49: 286
      CrossrefPubMed
    • 24c Sheng F.-T, Wang J.-Y, Tan W, Zhang Y.-C, Shi F. Org. Chem. Front. 2020; 7: 3967
      Crossref
    • 24d Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
      CrossrefPubMed
    • 24e Zheng C, You S.-L. ACS Cent. Sci. 2021; 7: 432
      CrossrefPubMed
  • 25 Dou P.-H, Chen Y, You Y, Wang Z.-H, Zhao J.-Q, Zhou M.-Q, Yuan W.-C. Adv. Synth. Catal. 2021; 363: 4047
    Crossref
  • 26 Zhao B.-L, Du D.-M. Adv. Synth. Catal. 2019; 361: 3412
    CrossrefPubMed

      • For selected reviews, see:
    • 27a Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662
      CrossrefPubMed
    • 27b Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res. 2014; 47: 2558
      CrossrefPubMed
  • 28 Zhao J.-Q, Zhou X.-J, Zhou Y, Xu X.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2018; 20: 909
    CrossrefPubMed
  • 29 Yue D.-F, Zhao J.-Q, Chen Y.-Z, Zhang X.-M, Xu X.-Y, Yuan W.-C. Adv. Synth. Catal. 2018; 360: 1420
    CrossrefPubMed
  • 30 Zhao J.-Q, Zhou X.-J, Chen Y.-Z, Xu X.-Y, Zhang X.-M, Yuan W.-C. Adv. Synth. Catal. 2018; 360: 2482
    Crossref