Synthesis 2019; 51(22): 4198-4204
DOI: 10.1055/s-0039-1690484
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Michael Addition–Cyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles

Estelle Silm
,
Sandra Kaabel
,
Ivar Järving
,
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@taltech.ee
› Author Affiliations
The authors thank the Estonian Ministry of Education and Research (Haridus- ja Teadusministeerium grant nos. IUT 19-32, IUT 19-9, and PUT 1468) and the Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013) for financial support.
Further Information

Publication History

Received: 15 May 2019

Accepted after revision: 27 June 2019

Publication Date:
11 July 2019 (eFirst)

Abstract

An asymmetric organocatalytic cascade reaction between cyclopentane-1,2-diones and alkylidene malononitriles affords highly substituted 4H-pyrans in moderate to high enantiomeric excess. The selective reduction of a bridged double bond leads to the formation of cis-substituted cyclopentanone with three contiguous stereogenic centres.

Supporting Information

 
  • References

  • 1 Present affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada

    • For recent reviews, see:
    • 2a Ciulla MG, Zimmermann S, Kumar K. Org. Biomol. Chem. 2019; 17: 413
    • 2b Indu S, Kaliappan KP. RSC Adv. 2018; 8: 21292
    • 2c Pellesier H. Adv. Synth. Catal. 2016; 358: 2194
    • 2d Lu L.-Q, Chen J.-R, Xiao W.-J. Acc. Chem. Res. 2012; 45: 1278

      For selected reviews, see:
    • 3a MacMillan DW. C. Nature 2008; 455: 304
    • 3b Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
    • 3c Chanda T, Zhao JC.-G. Adv. Synth. Catal. 2018; 360: 2
    • 3d Qin Y, Zhu L, Luo S. Chem. Rev. 2017; 117: 9433
  • 4 Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
    • 5a Benkovic SJ, Hammes-Schiffer S. Science 2003; 301: 1196
    • 5b Klinman JP, Offenbacher AR, Hu S. J. Am. Chem. Soc. 2017; 139: 18409
  • 6 Bui T, Barbas CF. III. Tetrahedron Lett. 2000; 41: 6951
  • 7 Chauhan P, Mahajan S, Enders D. Acc. Chem. Res. 2017; 50: 2809
  • 8 Rueping M, Volla CM. R, Bolte M, Raabe G. Adv. Synth. Catal. 2011; 353: 2853
  • 9 Rueping M, Sugiono E, Merino E. Chem. Eur. J. 2008; 14: 6329
  • 10 Franke PT, Richter B, Jørgensen KA. Chem. Eur. J. 2008; 14: 6317
  • 11 Nair DK, Menna-Barreto RF. S, daSilva EN. Jr, Mobin SM, Namboothiri IN. N. Chem. Commun. 2014; 50: 6973
  • 12 Ramireddy N, Abbaraju S, Ding D, Arman H, Zhao JC.-G. J. Heterocycl. Chem. 2017; 54: 677
  • 13 Rueping M, Kuenkel A, Fröhlich R. Chem. Eur. J. 2010; 16: 4173
  • 14 Ding D, Zhao C.-G. Tetrahedron Lett. 2010; 51: 1322
  • 15 Rueping M, Kuenkel A, Tato F, Bats JW. Angew. Chem. Int. Ed. 2009; 48: 3699
  • 16 Preegel G, Noole A, Ilmarinen K, Järving I, Kanger T, Pehk T, Lopp M. Synthesis 2014; 46: 2595
  • 17 Preegel G, Silm E, Kaabel S, Järving I, Rissanen K, Lopp M. Synthesis 2017; 49: 3118
  • 18 Desimoni G, Faita G, Quadrelli P. Chem. Rev. 2013; 113: 5924
  • 19 Preegel G, Ilmarinen K, Järving I, Kanger T, Pehk T, Lopp M. Synthesis 2015; 47: 3805
  • 20 Foloppe N, Fisher LM, Howes R, Potter A, Robertson AG. S, Surgenor AE. Bioorg. Med. Chem. 2006; 14: 4792
  • 21 Urbahns K, Horvath E, Stasch JP, Mauler F. Bioorg. Med. Chem. 2003; 13: 2637
  • 22 Wang J.-L, Dongxiang L, Zhang Z.-J, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 7124
  • 23 Ciulla MG, Zimmermann S, Kumal K. Org. Biomol. Chem. 2019; 17: 413
  • 24 Chauhan P, Mahajan S, Kaya U, Hack D, Enders D. Adv. Synth. Catal. 2015; 357: 253
  • 25 Probst N, Madarász Á, Valkonen A, Pápai I, Rissanen K, Neuvonen A, Pihko PM. Angew. Chem. Int. Ed. 2012; 51: 8495
  • 26 Rho HS, Oh SH, Lee JW, Lee JY, Chin J, Song CE. Chem. Commun. 2008; 10: 1208
  • 27 Wrobel J, Cook JM. Synth. Commun. 1980; 10: 333
  • 28 Vakulya B, Varga S, Csámpal A, Soós T. Org. Lett. 2005; 7: 1967
  • 29 Lee JW, Ryu TH, Oh JS, Bae HY, Jang HB, Song CE. Chem. Commun. 2009; 46: 7224
  • 30 Okino T, Hoashi Y, Takemoto Y. J. Am. Chem. Soc. 2003; 125: 12672
  • 31 Jiang X, Liu S, Yang S, Jing M, Xu L, Yu P, Wang Y, Yeung Y.-Y. Org. Lett. 2018; 20: 3259