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Synthesis 2016; 48(08): 1131-1138
DOI: 10.1055/s-0035-1560412
DOI: 10.1055/s-0035-1560412
paper
Asymmetric Synthesis of Spiro Tetrahydrothiophene-indan-1,3-diones via a Squaramide-Catalyzed Sulfa-Michael/Aldol Domino Reaction
Authors
Further Information
Publication History
Received: 01 February 2016
Accepted after revision: 02 February 2016
Publication Date:
15 February 2016 (online)
Abstract
A new asymmetric domino sulfa-Michael/aldol reaction of 2-arylidene-1,3-indandiones with 1,4-dithiane-2,5-diol catalyzed by a sub-mol% loading of a squaramide provides a direct access to tetrahydrothiophene bearing spiro indane-1,3-dione derivatives in excellent yields and good stereoselectivities.
Supporting Information
- Supporting information for this article is available online http://dx.doi.org/10.1055/s-0035-1560412.
Included are copies of the 1H and 13C NMR spectra 3a–j, 3a′, 3j′ and 4, NOSEY of 3a′
and 4a, and HPLC data of 3a′–j′, and CD measurement data.
- Supporting Information (PDF) (opens in new window)
-
References
- 1a Enders D. Grondal C. Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
- 1b Yu X. Wang W. Org. Biomol. Chem. 2008; 6: 2037
- 1c Grondal C. Jeanty M. Enders D. Nat. Chem. 2010; 2: 167
- 1d Moyano A. Rios R. Chem. Rev. 2011; 111: 4703
- 1e Albrecht Ł. Jiang H. Jørgensen KA. Angew. Chem. Int. Ed. 2011; 50: 8492
- 1f Grossmann A. Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 1g Pellissier H. Adv. Synth. Catal. 2012; 354: 237
- 1h Lu L.-Q. Chen J.-R. Xiao W.-J. Acc. Chem. Res. 2012; 45: 1278
- 1i Goudedranche S. Raimondi W. Bugaut X. Constantieux T. Bonne D. Rodriguez J. Synthesis 2013; 45: 1909
- 1j Volla MR. Atodiresei I. Rueping M. Chem. Rev. 2014; 114: 2390
- 2a Alemán J. Parra A. Jiang H. Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
- 2b Storer RI. Aciro C. Jones LH. Chem. Soc. Rev. 2011; 40: 2330
- 2c Chauhan P. Mahajan S. Kaya U. Hack D. Enders D. Adv. Synth. Catal. 2015; 357: 253
- 3a Loh CC. J. Hack D. Enders D. Chem. Commun. 2013; 49: 10230
- 3b Loh CC. J. Chauhan P. Hack D. Lehmann C. Enders D. Adv. Synth. Catal. 2014; 356: 3181
- 4a De Clercq PJ. Chem. Rev. 1997; 97: 1755
- 4b Zempleni J. Wijeratne SS. K. Hassan YI. Biofactors 2009; 35: 36
- 5 Johnson JW. Evanoff DP. Savard ME. Lange G. Ramadhar TR. Assoud A. Taylor NJ. Dmitrienko GI. J. Org. Chem. 2008; 73: 6970
- 6 Yoshimura Y. Watanabe M. Satoh H. Ashida N. Ijichi K. Sakata S. Machida H. Matsuda A. J. Med. Chem. 1997; 40: 2177
- 7a Yoshikawa M. Murakami T. Shimada H. Matsuda H. Yamahara J. Tanabe G. Muraoka O. Tetrahedron Lett. 1997; 38: 8367
- 7b Yuasa H. Takada J. Hashimoto H. Bioorg. Med. Chem. Lett. 2001; 11: 1137
- 7c Yoshikawa M. Morikawa T. Matsuda H. Tanabe G. Muraoka O. Bioorg. Med. Chem. 2002; 10: 1547
- 7d Matsuda H. Morikawa T. Yoshikawa M. Pure Appl. Chem. 2002; 74: 1301
- 8a Chauhan P. Mahajan S. Enders D. Chem. Rev. 2014; 114: 8807
- 8b Brandau S. Maerten E. Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 14986
- 8c Baricordi N. Benetti S. De Risi C. Fogagnolo M. Pollini GP. Zanirato V. Lett. Org. Chem. 2009; 6: 593
- 8d Luo G. Zhang S. Duan W. Wang W. Tetrahedron Lett. 2009; 50: 2946
- 8e Yu C. Zhang Y. Song A. Ji Y. Wang W. Chem. Eur. J. 2011; 17: 770
- 8f Duan S.-W. Li Y. Liu Y.-Y. Zou Y.-Q. Shi D.-Q. Xiao W. Chem. Commun. 2012; 5160
- 8g Ling J.-B. Su Y. Zhu H.-L. Wang G.-Y. Xu P.-F. Org. Lett. 2012; 14: 1090
- 8h Su Y. Ling J.-B. Zhang S. Xu P.-F. J. Org. Chem. 2013; 78: 11053
- 8i Meninno S. Croce G. Lattanzi A. Org. Lett. 2013; 15: 3436
- 8j Huang Y. Zheng C. Chai Z. Zhao G. Adv. Synth. Catal. 2014; 356: 579
- 8k Liang J.-J. Pan J.-Y. Xu D.-C. Xie J.-W. Tetrahedron Lett. 2014; 55: 6335
- 8l Li Y.-H. Zhao B.-L. Gao Y. Du D.-M. Tetrahedron: Asymmetry 2014; 25: 1513
- 8m Zhao B.-L. Liu L. Du D.-M. Eur. J. Org. Chem. 2014; 7850
- 8n Zhong Y. Ma S. Li B. Jiang X. Wang R. J. Org. Chem. 2015; 80: 6870
- 8o Hu Y.-J. Wang X.-B. Li S.-Y. Xie S.-S. Wang KD. G. Kong L.-Y. Tetrahedron Lett. 2015; 56: 105
- 8p Bharkavi C. Kumar SV. Perumal S. Synlett 2015; 26: 1665
- 9a Evans PA. Brandt TA. Tetrahedron Lett. 1996; 37: 1367
- 9b Clive DL. J. Kong X. Paul CC. Tetrahedron 1996; 52: 6085
- 9c Nicolaou KC. Montagnon T. Vassilikogiannakis G. Chem. Commun. 2002; 2478
- 9d Nicolaou KC. Montagnon T. Vassilikogiannakis G. Mathison CJ. N. J. Am. Chem. Soc. 2005; 127: 8872
- 9e Pizzirani D. Roberti M. Grimaudo S. Cristina AD. Pipitone RM. Tolomeo M. Recanatini M. J. Med. Chem. 2009; 52: 6936
- 10a Ramachary DB. Barbas III CF. Chem. Eur. J. 2004; 10: 5323
- 10b Ramachary DB. Chowdari NS. Barbas III CF. Synlett 2003; 1910
- 11a Ramachary DB. Anebouselvy K. Chowdari NS. Barbas III CF. J. Org. Chem. 2004; 69: 5838
- 11b Ramachary DB. Venkaiah C. Krishna PM. Chem. Commun. 2012; 48: 2252
- 11c Hu F. Wei Y. Shi M. Tetrahedron 2012; 68: 7911
- 11d Kuan H.-H. Chien C.-H. Chen K. Org. Lett. 2013; 15: 2880
- 11e Das U. Tsai Y.-L. Lin W. Org. Biomol. Chem. 2013; 11: 44
- 11f Anwar S. Li S.-M. Chen K. Org. Lett. 2014; 16: 2993
- 11g Chang Y.-P. Gurubrahamam R. Chen K. Org. Lett. 2015; 17: 2908
- 11h Zhang Y.-Y. Gurubrahamam R. Chen K. Adv. Synth. Catal. 2015; 357: 2457
- 11i Duan J. Cheng J. Li P. Org. Chem. Front. 2015; 2: 1048
- 11j Blümel M. Chauhan P. Vermeeren C. Dreier A. Lehmann C. Enders D. Synthesis 2015; 47: 3618
- 12a Hahn R. Raabe G. Enders D. Org. Lett. 2014; 16: 3636
- 12b Chauhan P. Urbanietz G. Raabe G. Enders D. Chem. Commun. 2014; 50: 6853
- 12c Urbanietz G. Atodiresei I. Enders D. Synthesis 2014; 46: 1261
- 12d Chauhan P. Mahajan S. Loh CC. J. Raabe G. Enders D. Org. Lett. 2014; 16: 2954
- 12e Loh CC. J. Chauhan P. Hack D. Lehmann C. Enders D. Adv. Synth. Catal. 2014; 356: 3181
- 12f Blümel M. Chauhan P. Hahn R. Raabe G. Enders D. Org. Lett. 2014; 16: 6012
- 12g Mahajan S. Chauhan P. Loh CC. J. Uzungelis S. Raabe G. Enders D. Synthesis 2015; 47: 1024
- 12h Chauhan P. Mahajan S. Raabe G. Enders D. Chem. Commun. 2015; 51: 2270
- 13 During the final stage of our work, an enantioselective synthesis of trans-configured spiro tetrahydrothiophene-indan-1,3-diones via a thiourea-catalyzed sulfa-Michael/Michael domino reaction was reported: Duan J. Cheng J. Li B. Qi F. Li P. Eur. J. Org. Chem. 2015; 6130
- 14 CCDC-1437740 (for rac-4) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: deposit@ccdc.cam.ac.uk.
- 15a Malerich JP. Hagihara K. Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416
- 15b Zhu Y. Malerich JP. Rawal VH. Angew. Chem. Int. Ed. 2010; 49: 153
- 16 Nie S.-Z. Hu Z.-P. Xuan Y.-N. Wang J.-J. Li X.-M. Yan M. Tetrahedron: Asymmetry 2010; 21: 2055
- 17 Benedek V. Varga S. Csámpai A. Soós T. Org. Lett. 2005; 7: 1967
- 18 Li H. Wang Y. Tang L. Deng L. J. Am. Chem. Soc. 2004; 126: 9906
For selected reviews on organocatalytic domino/cascade reactions, see:
For reviews on squaramide catalysts, see:
For a recent review, see:
For recent asymmetric syntheses, see:
For recent non-enantioselective syntheses, see:
For initial non-enantioselective syntheses, see:
For stereoselective reactions, see: