Synthesis of Chiral Spiro[oxindole-3,2′-pyrrolidine] Derivatives Integrated with Spiro Indane-1,3-dione and Trifluoromethyl Group Pharmacophores via Organocatalyzed Asymmetric [3+2] Annulation

Abstract

A mild and efficient organocatalyzed [3+2] cycloaddition of isatin-derived ketimines and 2-ylideneindane-1,3-diones has been realized. The resulting spiro[oxindole-3,2′-pyrrolidine]s bearing both a spiro indane-1,3-dione motif and a trifluoromethyl group were obtained in high yields with good diastereo- and enantioselectivities.

Key words

asymmetric synthesis - indane-1,3-dione - isatin-based ketimine - organocatalysis - spiro[oxindole-3,2′-pyrrolidine]

Publikationsverlauf

Eingereicht: 14. Oktober 2022

Angenommen nach Revision: 06. Dezember 2022

Accepted Manuscript online:
06. Dezember 2022

Artikel online veröffentlicht:
10. Januar 2023

• References

• 1 Ali MA, Ismail R, Choon TS, Yoon YK, Wei AC, Pandian S, Kumar RS, Osman H, Manogaran E. Bioorg. Med. Chem. Lett. 2010; 20: 7064
• 2 Gollner A, Rudolph D, Arnhof H, Bauer M, Blake SM, Boehmelt G, Cockroft XL, Dahmann G, Ettmayer P, Gerstberger T, Karolyi-Oezguer J, Kessler D, Kofink C, Ramharter J, Rinnenthal J, Savchenko A, Schnitzer R, Weinstabl H, Weyer-Czernilofsky U, Wunberg T, McConnell DB. J. Med. Chem. 2016; 59: 10147
• 3 Lindsley CW, Conn PJ, Wood MR, Hopkins CR, Melancon BJ, Poslusney MS. WO 2013071201, 2013
• 4 Kornet MJ, Thio AP. J. Med. Chem. 1976; 19: 892
• 5a Shyamsivappan S, Vivek R, Saravanan A, Arasakumar T, Subashini G, Suresh T, Shankar R, Mohan PS. Med. Chem. Commun. 2019; 10: 439
• 5b Kumar A, Gupta G, Bishnoi AK, Saxena R, Saini KS, Konwar R, Kumar S, Dwivedi A. Bioorg. Med. Chem. 2015; 23: 839
• 6 Girgis AS, Panda SS, Srour AM, Farag H, Ismail NS. M, Elgendy M, Abdel-Aziz AK, Katritzky AR. Org. Biomol. Chem. 2015; 13: 6619
• 7 Ranjith Kumar R, Perumal S, Senthilkumar P, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2009; 44: 3821
• 8 Karthikeyan K, Sivakumar PM, Doble M, Perumal PT. Eur. J. Med. Chem. 2010; 45: 3446
• 9 Murugan R, Anbazhagan S, Narayanan SS. Eur. J. Med. Chem. 2009; 44: 3272
• 10 Liu SF, Lin B, Xi YF, Zhou L, Lou LL, Huang XX, Wang XB, Song SJ. Org. Biomol. Chem. 2018; 16: 9430
• 11a Raj AA, Raghunathan R, SrideviKumarib MR, Raman N. Bioorg. Med. Chem. 2003; 11: 407
• 11b Babu AR. S, Raghunathan R, Mathivanan N, Omprabha G, Velmurugan D, Raghu R. Curr. Chem. Biol. 2008; 2: 312
• 12 Pandey RC, Toussaint MW, Stroshane RM, Kahta CC, Aszalos AA, Garretson AL, Wei TT, Byrne KM, Geoghegan RF. Jr, White RJ. J. Antibiot. 1981; 34: 1389
• 13 Sudhapriya N, Perumal PT, Balachandran C, Ignacimuthu S, Sangeetha M, Doble M. Eur. J. Med. Chem. 2014; 83: 190
• 14 Turroni S, Tolomeo M, Mamone G, Picariello G, Giacomini E, Brigidi P, Roberti M, Grimaudo S, Pipitone RM, Di Cristina A, Recanatini M. PLoS One 2013; 8: e57650
• 15a Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao G.-Q, Barluenga S, Mitchell HJ. J. Am. Chem. Soc. 2000; 122: 9939
• 15b Garcia-Castro M, Zimmermann S, Sankar MG, Kumar K. Angew. Chem. Int. Ed. 2016; 55: 7586
• 16a Yang Y, Zhu B, Zhu L, Jiang Y, Guo C.-L, Gu J, Ouyang Q, Du W, Chen Y.-C. Chem. Sci. 2021; 12: 11399
• 16b Trost BM, Jiao Z. J. Am. Chem. Soc. 2020; 142: 21645
• 16c Mao B, Liu H, Yan Z, Xu Y, Xu J, Wang W, Wu Y, Guo H. Angew. Chem. Int. Ed. 2020; 59: 11316
• 16d Vetica F, Bailey SJ, Kumar M, Mahajan S, von Essen C, Rissanen K, Enders D. Synthesis 2020; 52: 2038
• 16e Zhang H, Gao X, Jiang F, Shi W, Wang W, Wu Y, Zhang C, Shi X, Guo H. Eur. J. Org. Chem. 2020; 4801
• 16f Bdiri B, Zhou Z.-M. Tetrahedron Lett. 2017; 58: 4600
• 17a Liao J, Xu J, Wu Y, Hou Y, Guo H. Adv. Synth. Catal. 2022; 364: 1074
• 17b Winter M, Faust K, Himmelsbach M, Waser M. Org. Biomol. Chem. 2019; 17: 5731
• 17c Chen K.-H, Karanam P, Vagh SS, Liou Y.-C, Lin W. Chem. Commun. 2018; 54: 12702
• 17d Xu H, Sha F, Li Q, Wu X.-Y. Org. Biomol. Chem. 2018; 16: 7214
• 17e Duan J, Cheng J, Li P. Org. Chem. Front. 2015; 2: 1048

For selected reviews on trifluoromethyl groups, see:
• 18a Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
• 18b Merino E, Nevado C. Chem. Soc. Rev. 2014; 43: 6598
• 18c Egami H, Sodeoka M. Angew. Chem. Int. Ed. 2014; 53: 8294
• 18d Besset T, Poisson T, Pannecoucke X. Chem. Eur. J. 2014; 20: 16830
• 18e Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320

For a pioneer work on the use of N-2,2,2-trifluoroethylisatin ketamine as 1,3-dipolar precursor, see:
• 19a Ma M, Zhu Y, Sun Q, Li X, Su J, Zhao L, Zhao Y, Qiu S, Yan W, Wang K, Wang R. Chem. Commun. 2015; 51: 8789

For most recent examples, see:
• 19b Zhou X.-J, Zhao J.-Q, Lai Y.-Q, You Y, Wang Z.-H, Yuan W.-C. Chirality 2022; 34: 1019
• 19c Li T.-H, Du D.-M. Org. Biomol. Chem. 2022; 20: 817
• 19d Zhou P, Yi Y, Hua Y.-Z, Jia S.-K, Wang M.-C. Chem. Eur. J. 2022; 28: e202103688
• 19e Zhao J.-Q, Zhou S, Yang L, Du H.-Y, You Y, Wang Z.-H, Zhou M.-Q, Yuan W.-C. Org. Lett. 2021; 23: 8600
• 19f Wang R.-L, Jia S.-K, Guo Y.-J, Yi Y, Hua Y.-Z, Lu H.-J, Wang M.-C. Org. Biomol. Chem. 2021; 19: 8492
• 19g Liu S.-J, Mao Q, Zhan G, Qin R, Chen B.-H, Xue J, Luo M.-L, Zhao Q, Han B. Org. Biomol. Chem. 2021; 19: 467
• 19h He Y, Liu Y, Liu Y, Kou X.-X, Li Q.-Z, Li J.-H, Jiang H.-Z, Leng H.-J, Peng C, Li J.-L. Adv. Synth. Catal. 2020; 362: 2052
• 19i Yi Y, Hua Y.-Z, Lu H.-J, Liu L.-T, Wang M.-C. Org. Lett. 2020; 22: 2527
• 19j Zou C, Han Y, Zeng C, Zhang TY, Ye J, Song G. Chin. Chem. Lett. 2020; 31: 377
• 19k Gao X.-Y, Yan R.-J, Xiao B.-X, Du W, Albrecht L, Chen Y.-C. Org. Lett. 2019; 21: 9628
• 19l Wang C, Wen D, Chen H, Deng Y, Liu X, Liu X, Wang L, Gao F, Guo Y, Sun M, Wang K, Yan W. Org. Biomol. Chem. 2019; 17: 5514
• 19m Zhao X, Xiong J, An J, Yu J, Zhu L, Feng X, Jiang X. Org. Chem. Front. 2019; 6: 1989
• 19n Li B, Gao F, Feng X, Sun M, Guo Y, Wen D, Deng Y, Huang J, Wang K, Yan W. Org. Chem. Front. 2019; 6: 1567
• 19o Lin Y, Song Y.-X, Du D.-M. Adv. Synth. Catal. 2019; 361: 1064
• 20a Zhao M, Li F, Cheng Y, Wang Y, Zhou Z. Chin. J. Org. Chem. 2021; 41: 4039
• 20b Xiao Y, Wang Y, Zhou Z. Chin. J. Org. Chem. 2019; 39: 2203
• 20c Lv D, Zhao M, Wang Y, Zhou Z. Org. Biomol. Chem. 2019; 17: 9636
• 20d Zhang H, Wang Y, Zhou Z. Tetrahedron 2018; 74: 6071
• 20e Cui L, Wang Y, Fan Z, Li Z, Zhou Z. Asian J. Org. Chem. 2018; 7: 2490
• 20f Xiao Y, Jiang R, Wang Y, Zhou Z. Adv. Synth. Catal. 2018; 360: 1961
• 20g Cui L, Lv D, Wang Y, Li Z, Fan Z, Zhou Z. J. Org. Chem. 2018; 83: 4221
• 20h Chen S, Wang Y, Zhou Z. J. Org. Chem. 2016; 81: 11432
• 20i Zheng Y, Cui L, Wang Y, Zhou Z. J. Org. Chem. 2016; 81: 4340
• 20j Cui L, Wang Y, Zhou Z. RSC Adv. 2016; 6: 64474
• 21 CCDC-2190460 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures/?