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Synthesis 2015; 47(17): 2529-2537
DOI: 10.1055/s-0034-1380522
DOI: 10.1055/s-0034-1380522
special topic
Reactions of Sulfonium Salts with 2,3-Dioxopyrrolidine Derivatives: A Concise Synthesis of Spirocyclopropane
Further Information
Publication History
Received: 07 February 2015
Accepted after revision: 11 March 2015
Publication Date:
19 May 2015 (online)
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Abstract
An efficient base-promoted spirocyclopropanation of 2,3-dioxopyrrolidine derivatives with sulfonium salts is described. This reaction enables a novel concise access to polysubstituted spirocyclopropane derivatives in good yields and with a trans/cis ratio of up to >20:1 under mild conditions.
Key words
spiro compounds - spirocyclopropane - sulfur ylides - sulfonium salt - 2,3-dioxopyrrolidine - heterocyclesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380522.
- Supporting Information
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References
- 1a Sannigrahi M. Tetrahedron 1999; 55: 9007
- 1b Fraga BM. Nat. Prod. Rev. 2007; 24: 1350
- 1c Kotha S, Deb AC, Lahiri K, Manivannan E. Synthesis 2009; 165
- 1d Rosenberg S, Leino R. Synthesis 2009; 2651
- 1e Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
- 1f Rios R. Chem. Soc. Rev. 2012; 41: 1060
- 1g D’yakonov VD, Trapeznikova OA, Meijere AD, Dzhemilev UM. Chem. Rev. 2014; 114: 5775
- 1h Carreira EM, Fessard TC. Chem. Rev. 2014; 114: 8257
- 2a Alper PB, Meyers C, Lerchner A, Siegel DR, Carreira EM. Angew. Chem. Int. Ed. 1999; 38: 3186
- 2b Guérot C, Tchitchanov BH, Knust H, Carreira EM. Org. Lett. 2011; 13: 780
- 2c Burkhard JA, Wuitschik G, Plancher JM, Rogers-Evans M, Carreira EM. Org. Lett. 2013; 15: 4312
- 2d Burkhard J, Carreira EM. Org. Lett. 2008; 10: 3525
- 2e Burkhard JA, Guérot C, Knust H, Rogers-Evans M, Carreira EM. Org. Lett. 2010; 12: 1944
- 2f Burkhard JA, Guérot C, Knust H, Rogers-Evans M, Carreira EM. Org. Lett. 2012; 14: 66
- 3a Tian L, Hu XQ, Li YH, Xu PF. Chem. Commun. 2013; 49: 7213
- 3b Zhao S, Lin JB, Zhao YY, Liang YM, Xu PF. Org. Lett. 2014; 16: 1802
- 3c Gao TP, Lin JB, Hu XQ, Xu PF. Chem. Commun. 2014; 50: 8934
- 4a Wessjohann LA, Brandt W, Thiemann T. Chem. Rev. 2003; 103: 1625
- 4b Charette AB, Lebel H. J. Am. Chem. Soc. 1996; 118: 10327
- 4c Barrett AG. M, Kasdorf K. J. Am. Chem. Soc. 1996; 118: 11030
- 5a Wong HN. C, Hon MY, Tse CW, Yip YC, Tanko J, Hudlicky T. Chem. Rev. 1989; 89: 165
- 5b Kulinkovich OG. Chem. Rev. 2003; 103: 2597
- 5c Brackmann F, de Meijere A. Chem. Rev. 2007; 107: 4493
- 6a Maas G. Chem. Soc. Rev. 2004; 33: 183
- 6b Lebel H, Marcoux JF, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
- 6c Doyle MP, Forbes DC. Chem. Rev. 1998; 98: 911
- 6d Hoveyda AH, Evans DA, Fu GC. Chem. Rev. 1993; 93: 1307
- 7a Raveendran AE, Paul RR, Suresh E, Nair V. Org. Biomol. Chem. 2010; 8: 901
- 7b Xie H, Zu L, Li H, Wang J, Wang H. J. Am. Chem. Soc. 2007; 129: 10886
- 7c Uria J, Vicario JL, Badia D, Carrillo L, Reyes E, Pesquera A. Synthesis 2010; 701
- 7d Companyo X, Alba AN, Cardenas F, Moyano A, Rios RR. Eur. J. Org. Chem. 2009; 3075
- 7e McCooey SH, McCabe T, Connon SJ. J. Org. Chem. 2006; 71: 7494
- 7f Kojima S, Suzuki M, Watanabe A, Ohkata K. Tetrahedron Lett. 2006; 47: 9061
- 7g Ibrahem I, Zhao GL, Rios R, Vesely J, Sunden H, Dziedzic P, Cordova A. Chem. Eur. J. 2008; 14: 7867
- 7h Vesely J, Zhao GL, Bartoszewicz A, Cordova A. Tetrahedron Lett. 2008; 49: 4209
- 7i Terrasson V, van der Lee A, de Figueiredo RM, Campagne JM. Chem. Eur. J. 2010; 16: 7875
- 7j Russo A, Meninno S, Tedesco C, Lattanzi A. Eur. J. Org. Chem. 2011; 5096
- 7k Papageorgiou CD, de Dios MA. C, Ley SV, Gaunt MJ. Angew. Chem. Int. Ed. 2004; 43: 4641
- 8a Ye Y, Zheng C, Fan R. Org. Lett. 2009; 11: 3156
- 8b Wang H, Fan R. J. Org. Chem. 2010; 75: 6994
- 8c Miao CB, Zhang M, Tian ZY, Xi HT, Sun XQ, Yang HY. J. Org. Chem. 2011; 76: 9809
- 8d Lin S, Li M, Dong Z, Liang F, Zhang J. Org. Biomol. Chem. 2014; 12: 1341
- 8e Yoshimura A, Jones TN, Yusubov MS, Zhdankin VV. Adv. Synth. Catal. 2014; 356: 3336
- 8f Yoshimura A, Koski SR, Kastern BJ, Fuchs JM, Jones TN, Yusubova RY, Nemykin VN, Zhdankin VV. Chem. Eur. J. 2014; 20: 5895
- 9a Trost BM, Melvin LS. Sulfur Ylides . Academic Press; New York: 1976
- 9b Li AH, Dai LX, Aggarwal VK. Chem. Rev. 1997; 97: 2341
- 9c Dai LX, Hou XL, Zhou YG. Pure Appl. Chem. 1999; 71: 369
- 9d Aggarwal VK, Winn CL. Acc. Chem. Res. 2004; 37: 611
- 9e McGarrigle EM, Myers EL, Aggarwal VK. Chem. Rev. 2007; 107: 5841
- 9f Sun XL, Tang Y. Acc. Chem. Res. 2008; 41: 937
- 9g Lu LQ, Chen JR, Xiao WJ. Acc. Chem. Res. 2012; 45: 1278
- 9h Li GC, Wang LY, Huang Y. Chin. J. Chem. 2013; 33: 1900
- 10 Corey EJ, Chaykovsky MJ. J. Am. Chem. Soc. 1965; 87: 1353
- 11a Aggarwal VK, Abdel-Rahman H, Jones RV. H, Lee HY, Reid BD. J. Am. Chem. Soc. 1994; 116: 5973
- 11b Aggarwal VK, Ford JG, Thompson A, Jones RV. H, Standen MC. H. J. Am. Chem. Soc. 1996; 118: 7004
- 11c Aggarwal VK, Abdel-Rahman H, Fan L, Jones RV. H, Standen MC. H. Chem. Eur. J. 1996; 2: 1024
- 11d Aggarwal VK, Ford JG, Fonquerna S, Adams H, Jones RV. H, Fieldhouse R. J. Am. Chem. Soc. 1998; 120: 8328
- 11e Aggarwal VK, Alonso E, Fang GY, Ferrara M, Hynd G, Porcelloni M. Angew. Chem. Int. Ed. 2001; 40: 1433
- 11f Aggarwal VK, Alonso E, Bae I, Hynd G, Lydon KM, Palmer MJ, Patel M, Porcelloni M, Richardson J, Stenson RA, Studley JR, Vasse JL, Winn CL. J. Am. Chem. Soc. 2003; 125: 10926
- 11g Aggarwal VK, Bae I, Lee HY, Richardson J, Williams DT. Angew. Chem. Int. Ed. 2003; 42: 3274
- 11h Aggarwal VK, Grange E. Chem. Eur. J. 2006; 12: 568
- 11i Fang GY, Wallner OA, Blasio ND, Ginesta X, Harvey JN, Aggarwal VK. J. Am. Chem. Soc. 2007; 129: 14632
- 11j Fritz SP, Matlock JV, McGarrigle EM, Aggarwal VK. Chem. Eur. J. 2013; 19: 10827
- 11k Matlock JV, Fritz SP, Harrison SA, Coe DM, McGarrigle EM, Aggarwal VK. J. Org. Chem. 2014; 79: 10226
- 11l Illa O, Namutebi M, Saha C, Ostovar M, Chen CC, Haddow MF, Nocquet-Thibault S, Lusi M, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2013; 135: 11951
- 12a Ye LW, Sun XL, Zhu CY, Tang Y. Org. Lett. 2006; 8: 3853
- 12b Deng XM, Cai P, Ye S, Sun XL, Liao WW, Li K, Tang Y, Wu YD, Dai LX. J. Am. Chem. Soc. 2006; 128: 9730
- 12c Ye LW, Sun XL, Li CY, Tang Y. J. Org. Chem. 2007; 72: 1335
- 12d Zheng JC, Zhu CY, Sun XL, Tang Y, Dai LX. J. Org. Chem. 2008; 73: 6909
- 12e Wang QG, Deng XM, Zhu BH, Ye LW, Sun XL, Li CY, Zhu CY, Shen Q, Tang Y. J. Am. Chem. Soc. 2008; 130: 5408
- 12f Zhu BH, Zhou R, Zheng JC, Deng XM, Sun XL, Shen Q, Tang Y. J. Org. Chem. 2010; 75: 3454
- 12g Zhu BH, Zheng JC, Yu CB, Sun XL, Zhou YG, Shen Q, Tang Y. Org. Lett. 2010; 12: 504
- 13 Luo J, Wu B, Chen MW, Jiang GF, Zhou YG. Org. Lett. 2014; 16: 2578
- 14a Lu LQ, Cao YJ, Liu XP, An J, Yao CJ, Ming ZH, Xiao WJ. J. Am. Chem. Soc. 2008; 130: 6946
- 14b Lu LQ, Ming ZH, An J, Li C, Chen JR, Xiao WJ. J. Org. Chem. 2011; 77: 1072
- 14c An J, Lu LQ, Yang QQ, Wang T, Xiao WJ. Org. Lett. 2013; 15: 542
- 14d Cheng Y, Hu XQ, Gao S, Lu LQ, Chen JR, Xiao WJ. Tetrahedron 2013; 69: 3810
- 15a Loebach JL, Bennett DM, Danheiser RL. J. Am. Chem. Soc. 1998; 120: 9690
- 15b Gais HJ, Reddy LR, Babu GS, Raabe G. J. Am. Chem. Soc. 2004; 126: 4859
- 15c Schomaker JM, Pulgam VR, Borhan B. J. Am. Chem. Soc. 2004; 126: 13600
- 15d Xie PZ, Wang LY, Yang LH, Li EQ, Ma JZ, Huang Y, Chen RY. J. Org. Chem. 2011; 76: 7699
- 15e Kramer S, Skrydstrup T. Angew. Chem. Int. Ed. 2012; 51: 4681
- 15f Chen JR, Dong WR, Candy M, Pan FF, Jörres M, Bolm C. J. Am. Chem. Soc. 2012; 134: 6924
- 15g Kumar BS, Venkataramasubramanian V, Sudalai A. Org. Lett. 2012; 14: 2468
- 15h Chen MW, Cao LL, Ye ZS, Jiang GF, Zhou YG. Chem. Commun. 2013; 49: 1660
- 15i Chagarovsky AO, Budynina EM, Ivanova OA, Villemson EV, Rybakov VB, Trushkov IV, Melnikov MY. Org. Lett. 2014; 16: 2830
- 15j Gao F, Huang Y. Adv. Synth. Catal. 2014; 356: 2422
- 16a Kunz RK, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 3240
- 16b Hartikka A, Arvidsson PI. J. Org. Chem. 2007; 72: 5874
- 16c Zhao YH, Zhao G, Cao WG. Tetrahedron: Asymmetry 2007; 10: 7
- 16d Wang J, Liu X, Dong S, Lin L, Feng X. J. Org. Chem. 2013; 78: 6322
- 17a Cheng Y, An J, Lu LQ, Wang ZY, Chen JR, Xiao WJ. J. Org. Chem. 2011; 76: 281
- 17b Dou XW, Lu YX. Chem. Eur. J. 2012; 18: 8315
- 18a Greger JG, Yoon-Miller SJ. P, Bechtold NR, Flewelling SA, Macdonald JP, Downey CR, Cohen EA, Pelkey ET. J. Org. Chem. 2011; 76: 8203
- 18b Boiadjiev SE, Lightner DA. J. Org. Chem. 1998; 63: 6220
- 18c Hosseini M, Kringelum H, Murray A, Tønder JE. Org. Lett. 2006; 8: 2103
- 19 Feng ZQ, Chu FM, Guo ZR, Sun PY. Bioorg. Med. Chem. Lett. 2009; 19: 2270
- 20 Bosch J, Roca T, Catena JL, Llorens O, Pérez JJ, Lagunas C, Fernández AG, Miquel I, Fernández-Serrat A, Farrerons C. Bioorg. Med. Chem. Lett. 2000; 10: 1745
- 21 Peifer C, Selig R, Kinkel K, Ott D, Totzke F, Schächtele C, Heidenreich R, Röcken M, Schollmeyer D, Laufer S. J. Med. Chem. 2008; 51: 3814
- 22 Chen X, Zhu L, Fang L, Yan S, Lin J. RSC Adv. 2014; 4: 9926
- 23 CCDC 1045728 contains the supplementary crystallographic data of 3d for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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