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Synthesis 2014; 46(19): 2595-2600
DOI: 10.1055/s-0034-1378374
DOI: 10.1055/s-0034-1378374
paper
Enantioselective Organocatalytic Michael Addition of Cyclopentane-1,2-diones to Nitroolefins
Further Information
Publication History
Received: 30 April 2014
Accepted after revision: 07 June 2014
Publication Date:
15 July 2014 (online)
Abstract
Organocatalytic Michael additions of cyclopentane-1,2-dione to different nitroolefins have been investigated. Cyclopentane-1,2-dione undergoes an organocatalytic reaction with substituted nitroolefins giving 3-substituted products in good to high yields (48–97%) and good stereoselectivity (up to 76% ee).
Key words
Michael addition - asymmetric synthesis - asymmetric catalysis - enantioselectivity - electrophilic addition - ketonesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Pandolfi E, Schapiro V, Heguaburu V, Labora M. Curr. Org. Synth. 2013; 10: 2
- 1b Orloff HD. Chem. Rev. 1954; 54: 347
- 1c Marco-Contelles J, Molina MT, Anjum S. Chem. Rev. 2004; 104: 2857
- 1d Rubinov DB, Rubinova IL, Akhrem AA. Chem. Rev. 1999; 99: 1047
- 1e Alkanes and Cycloalkanes . Patai S, Rappoport Z. Wiley; Chichester: 1992
- 2a Heasley B. Eur. J. Org. Chem. 2009; 1477
- 2b Hudlicky T, Price JD. Chem. Rev. 1989; 89: 1467
- 2c Trost BM, Schroeder M. J. Am. Chem. Soc. 2000; 122: 3785
- 2d Wang Z, Reinus BJ, Dong G. J. Am. Chem. Soc. 2012; 134: 13954
- 2e Varea T, Alcalde A, Dicastillo CL, Arellano CR, Cossío FP, Asensio G. J. Org. Chem. 2012; 77: 6327
- 3a Ding Y, Girardet J.-L, Smith KL, Larson G, Brett P, Lai VC. H, Zhong W, Wu JZ. Bioorg. Med. Chem. Lett. 2005; 15: 675
- 3b Helmchen G, Ernst M, Paradies G. Pure Appl. Chem. 2004; 76: 495
- 3c Kurteva VB, Afonso CA. M. Chem. Rev. 2009; 109: 6809
- 3d Liu G, Shirley ME, Van K N, McFarlin RL, Romo D. Nat. Chem. 2013; 5: 1049
- 4a Niidu A, Paju A, Müürisepp A.-M, Järving I, Kailas T, Pehk T, Lopp M. Chem. Heterocycl. Compd. 2013; 48: 1751
- 4b Niidu A, Paju A, Eek M, Müürisepp A.-M, Pehk T, Lopp M. Tetrahedron: Asymmetry 2006; 17: 2678
- 4c Paju A, Oja K, Matkevitš K, Lumi P, Järving I, Pehk T, Lopp M. Heterocycles 2014; 88: 981
- 5a Taniguchi T, Tanabe G, Muraoka O, Ishibashi H. Org. Lett. 2008; 10: 197
- 5b Taniguchi T, Ishibashi H. Tetrahedron 2008; 64: 8773
- 5c Winkler CK, Stueckler C, Mueller NJ, Pressnitz D, Faber K. Eur. J. Org. Chem. 2010; 6354
- 5d Jõgi A, Ilves M, Paju A, Pehk T, Kailas T, Müürisepp A.-M, Lopp M. Tetrahedron: Asymmetry 2008; 19: 628
- 5e Paju A, Laos M, Jõgi A, Päri M, Jäälaid R, Pehk T, Kanger T, Lopp M. Tetrahedron Lett. 2006; 47: 4491
- 5f Paju A, Kanger T, Pehk T, Eek M, Lopp M. Tetrahedron 2004; 60: 9081
- 6a Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
- 6b Asymmetric Organocatalysis. In Topics in Current Chemistry. Vol. 291. List B. Springer; Berlin: 2009
- 6c Tsakos M, Kokotos CG. Tetrahedron 2013; 69: 10199
- 6d Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
- 7a Noole A, Sucman NS, Kabeshov MA, Kanger T, Macaev FZ, Malkov AV. Chem. Eur. J. 2012; 18: 14929
- 7b Noole A, Järving I, Werner F, Lopp M, Malkov A, Kanger T. Org. Lett. 2012; 14: 4922
- 7c Noole A, Ošeka M, Pehk T, Öeren M, Järving I, Elsegood MR. J, Malkov AV, Lopp M, Kanger T. Adv. Synth. Catal. 2013; 355: 829
- 7d Noole A, Ilmarinen K, Järving I, Lopp M, Kanger T. J. Org. Chem. 2013; 78: 8117
- 7e Žari S, Kailas T, Kudrjashova M, Öeren M, Järving I, Tamm T, Lopp M, Kanger T. Beilstein J. Org. Chem. 2012; 8: 1452
- 7f Žari S, Kudrjashova M, Pehk T, Lopp M, Kanger T. Org. Lett. 2014; 16: 1740
- 8a Zheng Z, Perkins BL, Ni B. J. Am. Chem. Soc. 2010; 132: 50
- 8b Hayashi Y, Itoh T, Ohkubo M, Ishikawa H. Angew. Chem. Int. Ed. 2008; 47: 4722
- 8c García-García P, Ladépêche A, Halder R, List B. Angew. Chem. Int. Ed. 2008; 47: 4719
- 8d Betancort JM, Barbas III CF. Org. Lett. 2001; 3: 3737
- 8e Sahoo G, Rahaman H, Madarász Á, Pápai I, Melarto M, Valkonen A, Pihko PM. Angew. Chem. Int. Ed. 2012; 51: 13144
- 9a Ramachary DB, Sakthidevi R, Shruthi K. Chem. Eur. J. 2012; 18: 8008
- 9b Ban S, Zhu X, Zhang Z, Xie H, Li Q. Eur. J. Org. Chem. 2013; 2977
- 9c Mandal T, Zhao C.-G. Tetrahedron Lett. 2007; 48: 5803
- 9d Ding D, Zhao C.-G. Tetrahedron Lett. 2010; 51: 1322
- 9e List B, Pojarliev P, Martin HJ. Org. Lett. 2001; 3: 2423
- 10a Rueping M, Kuenkel A, Frölich R. Chem. Eur. J. 2010; 16: 4173
- 10b Ding D, Zhao C.-G, Guo Q, Arman H. Tetrahedron 2010; 66: 4423
- 11 Li W, Liu X, Mao Z, Chen Q, Wang R. Org. Biomol. Chem. 2012; 10: 4767
- 12 Rueping M, Kuenkel A, Tato F, Bats JW. Angew. Chem. Int. Ed. 2009; 48: 3699
- 13 Paju A, Kanger T, Pehk TM, Lopp M. Tetrahedron 2002; 58: 7321
- 14 Reile I, Paju A, Kanger T, Järving I, Lopp M. Tetrahedron Lett. 2012; 53: 1476
- 15 Jang HB, Rho HS, Oh JS, Nam EH, Park SE, Bae HY, Song CE. Org. Biomol. Chem. 2010; 8: 3918
- 16 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
- 17 Noole A, Järving I, Werner F, Lopp M, Malkov A, Kanger T. Org. Lett. 2012; 14: 4922
- 18 Bae HY, Some S, Lee JH, Kim J.-Y, Song MJ, Lee S, Zhang YJ, Song CE. Adv. Synth. Catal. 2011; 353: 3196
- 19 Albrecht L, Dickmeiss G, Acosta FC, Rodríguez-Escrich C, Davis RI, Jørgensen KA. J. Am. Chem. Soc. 2012; 134: 2543
- 20 Lee JW, Ryu TH, Oh JS, Bae HY, Jang HB, Song CE. Chem. Commun. 2009; 7224
- 21 Wrobel J, Cook JM. Synth. Commun. 1980; 10: 333
- 22 Bharathiraja G, Sakthivel S, Sengoden M, Punniyamuthy T. Org. Lett. 2013; 15: 4996
Selected general reviews on cyclohexanes:
Selected general reviews on organocatalysis: