Synthesis 2020; 52(07): 1076-1086
DOI: 10.1055/s-0039-1690774
paper
© Georg Thieme Verlag Stuttgart · New York

Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction

Deborah A. dos Santos
a  Centre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil   Email: agcorrea@ufscar.br
b  Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
,
Allan R. da Silva
a  Centre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil   Email: agcorrea@ufscar.br
b  Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
,
Javier Ellena
c  São Carlos Institute of Physics, University of São Paulo, 13560-570, São Carlos, SP, Brazil
,
Cecilia C. P. da Silva
b  Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
,
Marcio W. Paixão
a  Centre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil   Email: agcorrea@ufscar.br
b  Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
,
a  Centre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil   Email: agcorrea@ufscar.br
b  Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
› Author Affiliations
The authors gratefully acknowledge Fundação de Amparo à Pesquisa do Estado de São Paulo (grants 2013/07600-3, 2014/50249-8, 2017/23867-0 and 2018/09961-7), GlaxoSmithKline, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Finance Code 001), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (grants 302634/2016-9, 305190/2017-2 and 429748/2018-3) for funding and fellowships.
Further Information

Publication History

Received: 05 November 2019

Accepted after revision: 01 December 2019

Publication Date:
16 December 2019 (online)


Abstract

Peptidomimetics containing an aziridine moiety have been reported as potent cysteine protease inhibitors. In this sense, the development of stereoselective and sustainable synthetic strategies to obtain three-membered N-heterocyclic compounds has gained importance in the last decades. In this work, an efficient method was designed to achieve highly functionalized aziridine peptidomimetics via a sequential reaction, which involves the organocatalytic aziridination of α,β-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethanol: water).

Supporting Information

 
  • References

  • 1 Aziridines and Epoxides in Organic Synthesis. Yudin AK. Weinheim; Wiley-VCH: 2006
  • 2 Paz MM, Zhang X, Lu J, Holmgren AA. Chem. Res. Toxicol. 2012; 25: 1502
  • 3 Corre C, Lowden PA. S. Chem. Commun. 2004; 8: 990
  • 4 Nakao Y, Fujita M, Warabi K, Matsunaga S, Fusetani N. J. Am. Chem. Soc. 2000; 122: 10462
  • 5 Schulz F, Gelhaus C, Degel B, Vicik R, Heppner S, Breuning A, Leippe M, Gut J, Rosenthal PJ, Schirmeister T. ChemMedChem 2007; 2: 1214
    • 6a Singh GS, Sudheesh S, Keroletswe N. ARKIVOC 2018; (i): 50
    • 6b Wang C. Synthesis 2017; 49: 5307
    • 6c Mao H, Jeong H, Yang J, Ha HJ, Yang JW. Chem. Eur. J. 2018; 24: 2370
    • 6d Glowacka IE, Trocha A, Wroblewski AE, Piotrowska DG. Beilstein J. Org. Chem. 2019; 15: 1722
    • 7a Lapinsky DJ. Three-Membered Ring Systems . In Progress in Heterocyclic Chemistry, Vol. 27. Gribble GW, Joule JA. Elsevier; Amsterdam: 2015: 61
    • 7b Rotstein BH, Zaretsky S, Rai V, Yudin AK. Chem. Rev. 2014; 114: 8323
    • 7c Meninno S, Lattanzi A. Catal. Today 2017; 285: 39
    • 7d Helene P. Lett. Org. Chem. 2018; 15: 171
    • 7e Roma E, Tosi E, Miceli M, Gasperi T. Asian J. Org. Chem. 2018; 7: 2357
  • 8 da Silva AR, dos Santos DA, Paixão MW, Corrêa AG. Molecules 2019; 24: 630
  • 9 Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
  • 11 Jiang J, Liu H, Lu C.-D, Xu Y.-J. Org. Lett. 2016; 18: 880
  • 12 Minakata S, Ando T, Nishimura M, Ryu I, Komatsu M. Angew. Chem. Int. Ed. 1999; 37: 3392
  • 13 Akiyama T, Suzuki T, Mori K. Org. Lett. 2009; 11: 2445
    • 14a Gupta AK, Mukherjee M, Wulff WD. Org. Lett. 2011; 13: 5866
    • 14b Gupta AK, Mukherjee M, Hu G, Wulff WD. J. Org. Chem. 2012; 77: 7932
  • 15 Bew SP, Liddle J, Hughes DL, Pesce P, Thurston SM. Angew. Chem. Int. Ed. 2017; 56: 5322
  • 16 Mukherjee M, Zhou Y, Dai Y, Gupta AL. K, Pulgam VR, Staples RJ, Wulff WD. Chem. Eur. J. 2017; 23: 2552
  • 17 Zhou Y, Gupta AK, Mukherjee M, Zheng L, Wulff WD. J. Org. Chem. 2017; 82: 13121
  • 18 Monteiro JL, Moreira NM, dos Santos DA, Paixão MW, Corrêa AG. Pure Appl. Chem. 2018; 90: 121
    • 19a Deobald AM, Corrêa AG, Rivera DG, Paixão MW. Org. Biomol. Chem. 2012; 10: 7681
    • 19b Deborah A, Maria A, Cornelio VE, Ávila RM. D, Cornea RC, Bernasconi GC. R, Paixão MW, Vieira PC, Corrêa AG. Bioorg. Med. Chem. 2017; 25: 4620
    • 20a Vesely J, Ibrahem I, Zhao G.-L, Rios R, Córdova A. Angew. Chem. Int. Ed. 2007; 46: 778
    • 20b Deiana L, Zhao G.-L, Lin S, Dziedzic P, Zhang Q, Leijonmarck H, Córdova A. Adv. Synth. Catal. 2010; 352: 3201
    • 20c Deina L, Dziedzic P, Zhao G.-L, Vesely J, Ibrahem I, Rios R, Sun J, Córdova A. Chem. Eur. J. 2011; 17: 7904
  • 21 Feu KA, Deobald AM, Narayanaperumal S, Corrêa AG, Paixão MW. Eur. J. Org. Chem. 2013; 5917
  • 22 Arai H, Sugaya N, Sasaki N, Makino K, Lectard S, Hamada Y. Tetrahedron Lett. 2009; 50: 3329
  • 23 Andraos J. Green Process Synth. 2019; 8: 324
  • 24 Corrêa AG, Paixão MW, Deobald AM, Rivera DG. Reaction: Organocatalytic Asymmetric Tandem Epoxidation-Passerini Reaction . In Green Syntheses, Vol. 1, Green Syntheses Series. CRC Press; Boca Raton: 2014: 139-148
  • 25 McElroy CR, Constantinou A, Jones LC, Summerton L, Clark JH. Green Chem. 2015; 17: 3111