Cycloaddition of γ-Hydroxy-α,β-unsaturated Ketones with Cyclic N-Sulfimines: Highly Stereoselective Synthesis of Polyheterotri­cyclic 1,3-Oxazolidine Derivatives

Abstract

A novel DBU-catalyzed cycloaddition of various γ-hydroxy-α,β-unsaturated ketones with cyclic N-sulfimines is described. The reaction is efficient under mild reaction conditions affording polyheterotricyclic 1,3-oxazolidine derivatives in moderate to high yields (43–82%).

Key words

γ-hydroxy-α,β-unsaturated ketones - cyclic N-sulfimines - cycloaddition - 1,3-oxazolidine - stereoselective

• References

• 1a Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
• 1b Sriharsha SN, Shashikanth S. Heterocycl. Commun. 2006; 12: 213
• 1c Li YJ, Ye F. Chin. Chem. Lett. 2006; 17: 891 ; Chem. Abstr. 2006, 986353
• 1d Yu L, Zhou W, Wang Z. Bioorg. Med. Chem. Lett. 2011; 21: 1541
• 1e Gudaprthi V, Bharathi K, Omprakash G. Asian J. Chem. 2011; 23: 765
• 1f Zhou XX, Dmitry MA, Sun P. PCT Int. Appl WO2011056126, 2011 ; Chem. Abstr. 2011, 590007.
• 1g Im WB, Choi SH, Park J.-Y, Choi SH, Finn J, Yoon S.-H. Eur. J. Med. Chem. 2011; 46: 1027
• 1h Fu Y, Yang L, Ye F, Gao S. J. Heterocycl. Chem. 2012; 49: 1235
• 1i Ye F, Liu C.-G, Wang X.-M, Fu Y, Gao S. Heterocycl. Commun. 2013; 19: 201
• 2a Bail ML, Pérard J, Atiken DJ, Bonin M, Husson HP. Tetrahedron Lett. 1997; 38: 7177
• 2b Heaney H, Papageorgiou G, Wilkins RF. Tetrahedron 1997; 53: 14381
• 2c Reddy SH. K, Lee S, Datta A, Georg GI. J. Org. Chem. 2001; 66: 8211
• 2d Yoo D, Oh JS, Kim YG. Org. Lett. 2002; 4: 1213
• 2e Choi WJ, Ahn HS, Kim HO, Kim S, Chun MW, Jeong LS. Tetrahedron Lett. 2002; 43: 6241
• 2f Huguenot F, Brigaud T. J. Org. Chem. 2006; 71: 2159
• 3a Agami C, Couty F. Eur. J. Org. Chem. 2004; 677
• 3b Pastor A, Adam W, Wirth T, Gabor T. Eur. J. Org. Chem. 2005; 3075
• 3c Wünnemann S, Fröhlich R, Hoppe D. Org. Lett. 2006; 8: 2455
• 4a Dai WM, Zhu HJ, Hao XJ. Tetrahedron: Asymmetry 1996; 7: 1245
• 4b Prasad KR. K, Joshi NN. J. Org. Chem. 1997; 62: 3770
• 4c Kang Y.-F, Liu L, Wang R, Zhou Y.-F, Yan W.-J. Adv. Synth. Catal. 2005; 347: 243
• 4d Wolf C, Xu H. Chem. Commun. 2011; 47: 3339
• 5a Michaelis DJ, Shaffer CJ, Yoon TP. J. Am. Chem. Soc. 2007; 129: 1866
• 5b Gandhi S, Bisai A, Bhanu Prasad BA, Singh VK. J. Org. Chem. 2007; 72: 2133
• 5c Martínez RF, Ávalos M, Babiano R, Cintas P, Jiménez JL, Light ME, Palacios JC, Pérez EM. S. Tetrahedron 2008; 64: 6377
• 5d Ávalos M, Babiano R, Cintas P, Jiménez JL, Light ME, Palacios JC, Pérez EM. S. J. Org. Chem. 2008; 73: 661
• 5e Chen D, Chen X, Du T, Kong L, Zhen R, Zhen S, Wen Y, Zhu G. Tetrahedron Lett. 2010; 51: 5131
• 5f Williamson KS, Yoon TP. J. Am. Chem. Soc. 2010; 132: 4570
• 5g Kim N.-S, Kang S.-Y, Lee S.-H. Bull. Korean Chem. Soc. 2010; 31: 553 ; Chem. Abstr. 2010, 416656
• 5h Elliott LD, Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2011; 13: 728
• 5i Williamson KS, Yoon TP. J. Am. Chem. Soc. 2012; 134: 12370
• 5j Ward AF, Wolfe JP. Org. Lett. 2011; 13: 4728
• 5k Jin Z, Wang X, Huang H, Liang X, Ye J. Org. Lett. 2011; 13: 564
• 5l Nimmagadda SK, Zhang Z, Antilla JC. Org. Lett. 2014; 16: 4098
• 6a Bergmann ED. Chem. Rev. 1953; 53: 309
• 6b Kumar GB, Patel HV, Shah AC, Trenkle M, Cardin CJ. Tetrahedron: Asymmetry 1996; 7: 3391
• 6c Galvez-Ruiz JC, Jaen-Gaspar JC, Castellanos-Arzola IG, Contreras R, Flores-Parra A. Heterocycles 2004; 63: 2269
• 6d Cintrat JC, Leat-Crest V, Parrain JL, Le Grognee E, Beaudet I, Quintard JP. Eur. J. Org. Chem. 2004; 4251
• 6e Huo CD, Wei R, Zhang W, Yang L, Liu ZL. Synlett 2005; 161
• 6f Braga AL, Sehnem JA, Lüdtke DS, Zeni G, Silveira CC, Marchi MI. Synlett 2005; 1331
• 6g Page PC. B, Parkes GA, Buckley BR, Heaney H, Gholizadeh M, Wailes JS. Tetrahedron Lett. 2008; 49: 6951
• 6h Martinez A, Sélambarom J. Tetrahedron Lett. 2011; 52: 1444
• 7a Ghorai MK, Ghosh K. Tetrahedron Lett. 2007; 48: 3191
• 7b Kang B, Miller AW, Goyal S, Nguyen ST. Chem. Commun. 2009; 3928
• 7c Wu X, Li L, Zhang J. Chem. Commun. 2011; 47: 7824
• 7d Maeda R, Ishibashi R, Kamaishi R, Hirotaki K, Furuno H, Hanamoto T. Org. Lett. 2011; 13: 6240
• 8 Fukata Y, Asano K, Matsubara S. Chem. Lett. 2013; 42: 355
• 9 Fukata Y, Asano K, Matsubara S. J. Am. Chem. Soc. 2013; 135: 12160
• 10 Kamal A, Sattur PB. Synthesis 1981; 272
• 11a Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Med. Res. Rev. 2005; 25: 186
• 11b Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Expert Opin. Ther. Pat. 2006; 16: 27
• 11c Woo LW. L, Purohit A, Potter BV. L. Mol. Cell. Endocrinol. 2011; 340: 175
• 11d Williams SJ. Expert Opin. Ther. Pat. 2013; 23: 79
• 12a Litvinas ND, Brodsky BH, Du Bois J. Angew. Chem. Int. Ed. 2009; 48: 4513
• 12b Luo Y, Carnell AJ, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 6762
• 12c Luo Y, Hepburn HB, Chotsaeng N, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 8309
• 12d Wang H, Jiang T, Xu M.-H. J. Am. Chem. Soc. 2013; 135: 971
• 12e Zhang L, Yu H, Yang Z, Liu H, Li Z, Guo J, Xiao Y, Guo H. Org. Biomol. Chem. 2013; 11: 8235
• 12f Yu H, Zhang L, Yang Z, Li Z, Zhao Y, Xiao Y, Guo H. J. Org. Chem. 2013; 78: 8427
• 12g Wang H, Xu M.-H. Synthesis 2013; 45: 2125
• 12h Hepburn HB, Chotsaeng N, Luo Y, Lam HW. Synthesis 2013; 45: 2649
• 12i Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C. Org. Lett. 2014; 16: 2538
• 12j Gao Z, Zhang L, Sun Z, Yu H, Xiao Y, Guo H. Org. Biomol. Chem. 2014; 12: 5691
• 12k Yang Z, Yu H, Zhang L, Wei H, Xiao Y, Chen L, Guo H. Chem. Asian J. 2014; 9: 313
• 12l Zhang H.-X, Nie J, Cai H, Ma J.-A. Org. Lett. 2014; 16: 2542
• 12m Yu H, Zhang L, Li Z, Liu H, Wang B, Xiao Y, Guo H. Tetrahedron 2014; 70: 340
• 13 CCDC 1054247 and 1054248 contain the supplementary crystallographic data for the product 3a. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
• 14 Wang J, Kong W.-G, Li F, Liu J, Shen Q, Liu L.-T, Zhao W.-X. Org. Biomol. Chem. 2015; 13: 5399
• 15a Litvinas ND, Brodsky BH, Bois JD. Angew. Chem. Int. Ed. 2009; 48: 4513
• 15b Yu H, Zhang L, Yang Z, Li Z, Zhao Y, Xiao Y, Guo H. J. Org. Chem. 2013; 78: 8427
• 16a Sada M, Ueno S, Asano K, Nomura K, Matsubara S. Synlett 2009; 5: 724
• 16b Li DR, Murugan A, Falck JR. J. Am. Chem. Soc. 2008; 130: 46
• 16c Greatrex BW, Kimber MC, Taylor DK, Tiekink ER. T. J. Org. Chem. 2003; 68: 4239