α-Sulfonyloxylation of 1,3-dicarbonyl compounds utilizing hypervalent iodine(iii) reagent: Construction of quaternary carbon center

References

• (a) Varvoglis, A. Synthesis. 1984, 9, 709–726. (b) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244–250. (c) Ochiai, M. Rev. Heteroat. Chem. 1989, 2, 92–111. (d) Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826–845. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123–1178. (f) Umemoto, T. Chem. Rev. 1996, 96, 1757–1778. (g) Varvoglis, A. Tetrahedron 1997, 53, 1179–1255. (h) Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927–10966. (i) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271–1287. (j) Koser, G. F. Aldrichimica Acta 2001, 34, 89–102. (k) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523–2584. (l) Wirth, T. Angew. Chem. Int. Chem. 2005, 44, 3656–3665. (m) Richardson, R. D.; Wirth, T. Angew. Chem. Int. Chem. 2006, 45, 4402–4404. (n) Dohi, T.; Morimoto, K.; Maruyama, A.; Kita, Y. Org. Lett. 2006, 8, 2017–2010. (o) Bose, D. S.; Idrees, M. J. Org. Chem. 2006, 71, 8261–8263. (p) Dohi, T.; Morimoto, K.; Takenaga, Naoko., Goto, A.; Maruyama, A.; Kiyono, Y.; Kita, Y. J. Org. Chem. 2007, 72, 109–116. (q) Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 25, 4229–4239. (r) Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 16, 2086–2099.
   Google Scholar
• (a) Koser, G. F.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1981, 46, 4324–4326. (b) Rebrovic, L.; Koser, G. F. J. Org. Chem. 1984, 49, 2462–2472. (c) Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari, M.; Sueda, T.; Goto, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 7716–7730. (d) Dauban, P.; Dodd, R. H. Synlett 2003, 11, 1571–1586.
   Google Scholar
• (a) Takata, T.; Tajima, R.; Ando, W. J. Org. Chem. 1983, 48, 4764–4766. (b) Kita, Y.; Egi, M.; Ohtsubo, M.; Saiki, T.; Takada, T.; Tohma, H. Chem. Commun. 1996, 2225–2227. (c) Akai, S.; Okuno, T.; Takada, T.; Tohma, H.; Kita, Y. Heterocycles 1996, 42, 47–51. (d) Tohma, H.; Watanabe, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Heterocycles 1999, 51, 1785–1788. (e) Kita, Y.; Egi, M; Takada, T.; Tohma, H. Synthesis 1999, 5, 885–897. (f) Chen, L. C.; Wang, H. M.; Kang, I. J. Heterocycles 1999, 51, 1437–1441. (g) Justik, M. W.; Koser, G. F. Molecules 2005, 10, 217–225.
   Web of Science ®Google Scholar
• (a) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J. Org. Chem. 1995, 60, 7144–7148. (b) Takada, T.; Arisawa, M.; Gyoten, M.; Hamada, R.; Tohma, H.; Kita, Y. J. Org. Chem. 1998, 63, 7698–7706. (c) Krikorian, D.; Tarpanov, V.; Parushev, S.; Mechkarova, P. Synthetic Commun. 2000, 30, 2833–2846.
   Web of Science ®Google Scholar
• (a) Koser, G. F.; Wettach, R. H.; Smith, C. S. J. Org. Chem. 1980, 45, 1543–1544. (b) Zhdankin, V. V.; Persichini III, P. J.; Cui, R.; Jin Y., Synlett 2000, 5, 0719– 0721. (c) Ochiai, M. J. Organometallic Chem. 2000, 611, 494–508. (d) Ren, K.; Malpert, J. H.; Gu, H.; Li, H. Y.; Neckers, D. C. Tetrahedron 2002, 58, 5267–5273.
   Web of Science ®Google Scholar
• (a) Moriarty, R. M.; Prakash, O.; Duncan, M. P. Synthesis 1985, 10, 943–944. (b) De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974–6977. (c) Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew. Chem. Int. Ed. 2000, 39, 1306–1308. (d) Lee, J. C.; Lee, J. Y.; Lee, S.J. Tetrahedron Lett. 2004, 45, 4939–4941. (e) Karade, N. N.; Tiwari, G. B.; Huple, D. B. Synlett 2005, 13, 2039–2042. (f) Guilbault, A. A., Legault, C. Y. ACS Catalysis 2012, 2, 219–222. (g) Guilbault, A. A., Basdevant, B., Wanie, V., Legault, C. Y. J. Org. Chem. 2012, 77, 11283–11295. (h) Basdevant, B., Legault, C. Y. Organic letters, 2015, 17, 4918–4921.
   Google Scholar
• (a) Ling, X.; Xiong, Y.; Zhang, S.; Huang, R.; Zhang, X. Chin. Chem. Lett. 2013, 24, 45–48. (b) Shen, H.; Zhang, X.; Liu, Q.; Pan, J.; Hu, W.; Xiong, Y.; Zhu, X. Tetrahedron Lett. 2015, 56, 5628–5631. (c) Shen, H.; Li, J.; Liu, Q.; Pan, J.; Huang, R.; Xiong, Y. J. Org. Chem. 2015, 80, 7212–7218. (d) Zhang, X.; Huang, R.; Marrot, J.; Coeffard, V.; Xiong, Y. Tetrahedron 2015, 71, 700–708. (e) Shen, H.; Deng, Q.; Liu, R.;, F, Y.; Zheng, C.; Xiong, Y. Org. Chem. Front. 2017, 4, 1806–1811.
   Web of Science ®Google Scholar
• (a) Koser, G. F.; Wettach, R. H. J. Org. Chem. 1976, 41, 3609–3611. (b) Koser, G. F.; Relenyi, A. G.; Kalos, A. N.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1982, 47, 2487–2489. (c) Moriaraty, R. M.; Penmasta, R.; Awasthi, A. K.; Epa, W. R.; Prakash, I. J. Org. Chem. 1989, 54, 1101–1104. (d) Bovonsombat, P.; Angara, G. J.; NcNelis, E. Tetrahedron Lett. 1994, 35, 6787–6790. (e) Lee, J. C.; Park, H. J.; Park, J. Y. Tetrahedron Lett. 2002, 43, 5661–5663. (f) Prakash, O.; Pannu, K.; Prakash, R.; Batra, A. Molecules 2006, 11, 523–527.
   Web of Science ®Google Scholar
• (a) Koser, G. F.; Wettach, R. H. J. Org. Chem. 1977, 42, 1476–1578. (b) Yamamoto, Y.; Togo, H. Synlett 2005, 16, 2486–2488. (c) Jalalian, N.; and Olofsson, B. Org. Synth. 2013, 90, 1–9.
   Web of Science ®Google Scholar
• (a) Lee, J. C.; Choi, J. H. Synlett 2001, 2, 0234–0235. (b) Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 2874–2877. (c) Moroda, A.; , Togo H. Tetrahedron 2006, 62, 12408–12414.
   Google Scholar
• (a) Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Shiro, M.; Kita, Y. Chem. Commun. 2005, 2205–2207. (b) Yu, J.; Cui, J.; Hou, X. S.; Liu, S. S.; Gao, W. C.; Jiang, S.; Tian, J.; , Zhang C. Tetrahedron: Asymmetry 2011, 22, 2039–2055 (c) Zhang, B.; Han, L.; Hu, J.; Yan, J. Tetrahedron Lett. 2014, 55, 5851–5854.
   Web of Science ®Google Scholar
• Nabana, T.; Togo, H. J. Org. Chem. 2002, 67, 4362–4365.
   PubMed Web of Science ®Google Scholar
• Merritt, E. A.; Carneiro, V. M. T.; Silva, L. F., Jr.; Olofsson, B. J. Org. Chem. 2010, 75, 7416–7419.
   PubMed Web of Science ®Google Scholar
• (a) Moriarty, R. M.; Vaid, R. K.; Hopkins, T. E.; Vaid, B. K.; Prakash, O. Tetrahedron Lett. 1990, 31, 201–204. (b) Prakash, O.; Rani, N.; Sharma, P. K. Synlett 1994, 221–227. (c) Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles 1994, 38, 409–430. (d) Lee, J. C.; Jin, Y. S. Synthetic commun. 1999, 29, 2769–2774. (e) Lee, J. C.; Kim, S.; Shin, W. C. Synthetic Commun. 2000, 30, 4271–4275. (g) Uneno, M.; Togo, H. Synthesis 2004, 16, 2673–2677.
   Web of Science ®Google Scholar
• (a) Moriarty, R. M.; Vaid, B. K.; Duncan, M. P.; Levy, S. G.; Prakash, O.; Goyal, S. Synthesis 1992, 9, 845–846. (b) Prakash, O.; Goyal, S. Synthesis 1992, 7\, 629–630. (c) Kita, Y.; Watanabe, H.; Egi, M.; Saiki, T.; Fukuoka, Y.; Tohma, H. J. Chem. Soc., Perkin Trans. 1, 1998, 635–636. (d) Kita, Y.; Egi, M.; Tohma, H. Chem. Commun. 1999, 2, 143–144.
   Google Scholar
• (a) Herrero, M. T.; Tellitu, I.; Dom´ınguez, E.; Herna´ndez, S.; Moreno, I.; SanMartı´ n R., Tetrahedron 2002, 58, 8581–8589. (b) John, O. R. S.; Killeen, N. M.; Knowles, D. A.; Yau, S. C.; Bagley, M. C.; Tomkinson, N. C. O. Org. Lett. 2007, 9, 4009–4012. (c) Yamamoto, Y.; Kawano, Y.; Toyb, P. H.; Togoa, H. Tetrahedron 2007, 63, 4680–4687.
   Web of Science ®Google Scholar
• Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244–12245.
   PubMed Web of Science ®Google Scholar
• Lodaya, J. S.; Koser, G. F. J. Org. Chem. 1988, 53, 210–212.
   Web of Science ®Google Scholar
• (a) Ma, H.; He, Y.; Huang, R. F.; Zhang, X. H.; Pan, J.; Li, J. Q.; He, C.; Ling, X. G.; Wang, X. L.; Xiong, Y. Chin. Chem. Lett. 2014, 25, 1327–1330. (b) Akula, R.; Xiong, Y.; , Ibrahim H. RSC Adv. 2013, 3, 10731–10735.
   Web of Science ®Google Scholar
• The asymmetric version has been reported, and the racemic one keeps unreported until now which utilizes isolated HTIBs as sulfonyloxylation reagents. For asymmetric version, see: Feng, Y. Y.; Huang, R. F.; Hu, L. Z.; Xiong, Y.; Coeffard, V. Synthesis 2016, 48, 2637–2644.
   Web of Science ®Google Scholar