Enantioselective Synthesis of Dispirooxindole Derivatives via Asymmetric Catalytic Cascade Reactions

Dedicated to Prof. Guo-Qiang Lin for his 80^th birthday.

Abstract

A series of optically active 3,3′-pyrrolidinyl-dispirooxindole derivatives containing a CF₃ moiety have been efficiently constructed through asymmetric catalytic cascade reactions catalyzed by cinchona-derived bifunctional squaramide catalyst, bearing four contiguous stereogenic centers, two of which are vicinal spiro-stereocenters. Additionally, a wide range of substituted products were achieved with moderate to high yields (up to 99% yield) and excellent stereoselectivities (up to >20:1 dr for all cases and up to 99% ee).

Key words

organocatalysis - dispirooxindole - cascade reactions - four contiguous stereogenic centers - new substrates

Publication History

Received: 16 December 2022

Accepted after revision: 22 January 2023

Accepted Manuscript online:
22 January 2023

Article published online:
27 February 2023

• References


For reviews, see:
• 1a Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
• 1b Rios R. Chem. Soc. Rev. 2012; 41: 1060
• 1c Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
• 1d Hiesinger K, Dar’in D, Proschak E, Krasavin MS. J. Med. Chem. 2021; 64: 150

For reviews and examples, see:
• 2a Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck H.-P, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
• 2b Babu SA, Padmavathi R, Aslam NA, Rajkumar V. Stud. Nat. Prod. Chem. 2015; 46: 227
• 2c Mali PR, Rao LC, Bangade VM, Shirsat PK, George SA, Babu NJ, Meshram HM. New J. Chem. 2016; 40: 2225
• 3 Antonchick AP, Gerding-Reimers C, Catarinella M, Schürmann M, Preut H, Ziegler S, Rauh D, Waldmann H. Nat. Chem. 2010; 2: 735
• 4 Arun Y, Bhaskar G, Balachandran C, Ignacimuthu S, Perumal PT. Bioorg. Med. Chem. Lett. 2013; 23: 1839
• 5 Velikorodov AV, Ionova VA, Degtyarev OV, Sukhenko LT. Pharm. Chem. J. 2013; 46: 715
• 6 Babu AR. S, Raghunathan R, Mathivanan N, Omprabha G, Velmurugan D, Raghu R. Curr. Chem. Biol. 2008; 2: 312

For reviews, see:
• 7a Luo Y.-C, Zhang H.-H, Wang Y, Xu P.-F. Acc. Chem. Res. 2010; 43: 1317
• 7b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
• 7c Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
• 7d Cheng D.-J, Ishihara Y, Tan B, Barbas CF. III. ACS Catal. 2014; 4: 743
• 7e Xie X, Huang W, Peng C, Han B. Adv. Synth. Catal. 2018; 360: 194
• 7f Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
• 8a Liu H, Dou G.-L, Shi D.-Q. J. Comb. Chem. 2010; 12: 292
• 8b Lanka S, Thennarasu S, Perumal PT. Tetrahedron Lett. 2014; 55: 2585
• 8c Suman K, Srinu L, Thennarasu SL. Org. Lett. 2014; 16: 3732
• 9a Xiao J.-A, Zhang H.-G, Liang S, Ren J.-W, Yang H, Chen X.-Q. J. Org. Chem. 2013; 78: 11577
• 9b Xu Q, Wang D, Wei Y, Shi M. ChemistryOpen 2014; 3: 93
• 9c Almansour AI, Arumugam N, Kumar RS, Periyasami G, Ghabbour HA, Fun H.-K. Molecules 2015; 20: 780
• 9d Lin B, Zhang W.-H, Wang D.-D, Gong Y, Wei Q.-D, Liu X.-L, Feng T.-T, Zhou Y, Yuan W.-C. Tetrahedron 2017; 73: 5176
• 9e Feng T.-T, Gong Y, Wei Q.-D, Wang G.-L, Liu H.-H, Tian M.-Y, Liu X.-L, Chen Z.-Y, Zhou Y. J. Heterocycl. Chem. 2018; 55: 1136
• 10a Dai W, Jiang X.-L, Wu Q, Shi F, Tu S.-J. J. Org. Chem. 2015; 80: 5737
• 10b Zhao K, Zhi Y, Li X.-Y, Puttreddy R, Rissanen K, Enders D. Chem. Commun. 2016; 52: 2249
• 10c Huang W.-J, Chen Q, Lin N, Long X.-W, Pan W.-G, Xiong Y.-S, Weng J, Lu G. Org. Chem. Front. 2017; 4: 472
• 10d Zhi Y, Zhao K, Essen C, Rissanen K, Enders D. Synlett 2017; 28: 2876
• 10e He Q, Du W, Chen Y.-C. Adv. Synth. Catal. 2017; 359: 3782
• 10f Lin Y, Zhao B.-L, Du D.-M. J. Org. Chem. 2018; 83: 7741

For selected examples, see:
• 11a Li B.-Y, Gao F.-Y, Feng X, Sun M.-M, Guo Y.-F, Wen D.-W, Deng Y.-B, Huang J.-Q, Wang K.-R, Yan W.-J. Org. Chem. Front. 2019; 6: 1567
• 11b Liu X, Lu D.-M, Wu J.-H, Tan J.-P, Jiang C.-H, Gao G.-W, Wang T.-L. Adv. Synth. Catal. 2020; 362: 1490
• 11c 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
• 11d You Y, Lu W.-Y, Wang Z.-H, Chen Y.-Z, Xu X.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2018; 20: 4453
• 11e Zhao B.-L, Du D.-M. Adv. Synth. Catal. 2019; 361: 3412
• 12a Ma M.-X, Zhu Y.-Y, Sun Q.-T, Li X.-Y, Su J.-H, Zhao L, Zhao Y.-Y, Qiu S, Yan W.-J, Wang K.-R, Wang R. Chem. Commun. 2015; 51: 8789
• 12b Sun Q.-T, Li X.-Y, Su J.-H, Zhao L, Ma M.-X, Zhu Y.-Y, Zhao Y.-Y, Zhu R.-R, Yan W.-J, Wang K.-R, Wang R. Adv. Synth. Catal. 2015; 357: 3187
• 12c Gui H.-Z, Wei Y, Shi M. Chem. Asian J. 2020; 15: 1225

For reviews, see:
• 13a Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 13b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 13c Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
• 13d Cametti M, Crousse B, Metrangolo P, Milani R, Resnati G. Chem. Soc. Rev. 2012; 41: 31
• 13e Smits R, Cadicamo CD, Burgerc K, Koksch B. Chem. Soc. Rev. 2008; 37: 1727
• 13f Wang J, Rosell MS, Aceña JL, Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
• 14a Wang Y, Han R.-G, Zhao Y.-L, Yang S, Xu P.-X, Dixon DJ. Angew. Chem. Int. Ed. 2009; 48: 9834
• 14b Liu J.-Y, Zhao J, Zhang J.-L, Xu P.-F. Org. Lett. 2017; 19: 1846
• 14c Zhao C.-G, Feng Z.-T, Xu G.-Q, Gao A, Chen J.-W, Wang Z.-Y, Xu P.-F. Angew. Chem. Int. Ed. 2020; 59: 3058
• 14d Ji D.-S, Luo Y.-C, Hu X.-Q, Xu P.-F. Org. Lett. 2020; 22: 1028
• 14e Zhang J.-L, Ma R, Zhao H.-H, Xu P.-F. Chem. Commun. 2022; 58: 3493
• 15a Zhang J.-L, Liu J.-Y, Xu G.-Q, Luo Y.-C, Lu H, Tan C.-Y, Hu X.-Q, Xu P.-F. Org. Lett. 2021; 23: 3287
• 15b Zhang J.-L, Ye W.-L, Zhang J, Hu X.-Q, Xu P.-F. Org. Lett. 2021; 23: 5033