Communication
Chiral Tertiary Sulfonium Salts as Effective Catalysts for Asymmetric Base-Free Neutral Phase-Transfer Reactions
Shiyao Liu,
Prof. Dr. Keiji Maruoka,
Prof. Dr. Seiji Shirakawa,
Shiyao Liu
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1–14 Bunkyo-machi, Nagasaki, 852-8521 Japan
Search for more papers by this authorProf. Dr. Keiji Maruoka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Seiji Shirakawa
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1–14 Bunkyo-machi, Nagasaki, 852-8521 Japan
Search for more papers by this authorShiyao Liu,
Prof. Dr. Keiji Maruoka,
Prof. Dr. Seiji Shirakawa,
Shiyao Liu
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1–14 Bunkyo-machi, Nagasaki, 852-8521 Japan
Search for more papers by this authorProf. Dr. Keiji Maruoka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Seiji Shirakawa
Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University, 1–14 Bunkyo-machi, Nagasaki, 852-8521 Japan
Search for more papers by this authorGraphical Abstract
Sulfonium catalyst: Whereas chiral quaternary ammonium and phosphonium salts are commonly used for asymmetric organocatalysis, chiral tertiary sulfonium salts have not been employed for such purposes. It is now shown that chiral bifunctional trialkylsulfonium salts catalyze the enantioselective conjugate addition of 3-substituted oxindoles to maleimides under base-free neutral phase-transfer conditions.
Abstract
Although chiral quaternary ammonium and phosphonium salts are commonly used for asymmetric organocatalysis, the catalytic ability of chiral tertiary sulfonium salts has yet to be demonstrated in asymmetric synthesis. Herein, we show that chiral bifunctional trialkylsulfonium salts catalyze highly enantioselective conjugate additions of 3-substituted oxindoles to maleimides under base-free neutral phase-transfer conditions.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie201612328-sup-0001-misc_information.pdf30.7 MB | Supplementary |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1For examples of chiral quaternary ammonium salts, see:
- 1aS. Colonna, R. Fornasier, J. Chem. Soc. Perkin Trans. 1 1978, 371;
- 1bS. Juliá, A. Ginebreda, J. Guixer, A. Tomás, Tetrahedron Lett. 1980, 21, 3709;
- 1cU.-H. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446;
- 1dM. Masui, A. Ando, T. Shioiri, Tetrahedron Lett. 1988, 29, 2835;
- 1eM. J. O'Donnell, W. D. Bennett, S. Wu, J. Am. Chem. Soc. 1989, 111, 2353;
- 1fB. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595;
- 1gE. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414;
- 1hT. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519;
- 1iS.-s. Jew, B.-S. Jeong, M.-S. Yoo, H. Huh, H.-g. Park, Chem. Commun. 2001, 1244;
- 1jT. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 9539;
- 1kS. Arai, R. Tsuji, A. Nishida, Tetrahedron Lett. 2002, 43, 9535;
- 1lM. Kitamura, S. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2005, 44, 1549; Angew. Chem. 2005, 117, 1573;
- 1mS. E. Denmark, N. D. Gould, L. M. Wolf, J. Org. Chem. 2011, 76, 4260;
- 1nM. Waser, K. Gratzer, R. Herchl, N. Müller, Org. Biomol. Chem. 2012, 10, 251;
- 1oH.-Y. Wang, J.-X. Zhang, D.-D. Cao, G. Zhao, ACS Catal. 2013, 3, 2218;
- 1pJ. Novacek, M. Waser, Eur. J. Org. Chem. 2014, 802.
- 2For examples of chiral quaternary phosphonium salts, see:
- 2aK. Manabe, Tetrahedron Lett. 1998, 39, 5807;
- 2bR. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. Int. Ed. 2008, 47, 9466; Angew. Chem. 2008, 120, 9608;
- 2cD. Uraguchi, Y. Asai, Y. Seto, T. Ooi, Synlett 2009, 658;
- 2dC.-L. Zhu, F.-G. Zhang, W. Meng, J. Nie, D. Cahard, J.-A. Ma, Angew. Chem. Int. Ed. 2011, 50, 5869; Angew. Chem. 2011, 123, 5991;
- 2eX. Wu, Q. Liu, Y. Liu, Q. Wang, Y. Zhang, J. Chen, W. Cao, G. Zhao, Adv. Synth. Catal. 2013, 355, 2701;
- 2fS. Shirakawa, K. Koga, T. Tokuda, K. Yamamoto, K. Maruoka, Angew. Chem. Int. Ed. 2014, 53, 6220; Angew. Chem. 2014, 126, 6334.
- 3For recent reviews on asymmetric phase-transfer catalysis, see:
- 3aM. J. O'Donnell, Aldrichimica Acta 2001, 34, 3;
- 3bT. Ooi, K. Maruoka, Acc. Chem. Res. 2004, 37, 526;
- 3cT. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 4222; Angew. Chem. 2007, 119, 4300;
- 3d Asymmetric Phase-Transfer Catalysis (Ed.: ), Wiley-VCH, Weinheim, 2008;
- 3eS.-s. Jew, H.-g. Park, Chem. Commun. 2009, 7090;
- 3fT. Werner, Adv. Synth. Catal. 2009, 351, 1469;
- 3gD. Enders, T. V. Nguyen, Org. Biomol. Chem. 2012, 10, 5327;
- 3hJ. Novacek, M. Waser, Eur. J. Org. Chem. 2013, 637;
- 3iS. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2013, 52, 4312; Angew. Chem. 2013, 125, 4408;
- 3jS. Kaneko, Y. Kumatabara, S. Shirakawa, Org. Biomol. Chem. 2016, 14, 5367;
- 3kS. Liu, Y. Kumatabara, S. Shirakawa, Green Chem. 2016, 18, 331.
- 4For reviews on chiral sulfonium salts, see:
- 4aA. Padwa, S. F. Hornbuckle, Chem. Rev. 1991, 91, 263;
- 4bO. Meyer, P. C. Cagle, K. Weickhardt, D. Vichard, J. A. Gladysz, Pure Appl. Chem. 1996, 68, 79;
- 4cV. K. Aggarwal, Synlett 1998, 329;
- 4dL.-X. Dai, X.-L. Hou, Y.-G. Zhou, Pure Appl. Chem. 1999, 71, 369;
- 4eV. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611;
- 4fY. Tang, S. Ye, X.-L. Li, Synlett 2005, 2720;
- 4gE. M. McGarrigle, E. L. Myers, O. Illa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841;
- 4hX.-L. Sun, Y. Tang, Acc. Chem. Res. 2008, 41, 937.
- 5For examples of chiral sulfonium salts in organic synthesis, see:
- 5aN. Furukawa, Y. Sugihara, H. Fijihara, J. Org. Chem. 1989, 54, 4222;
- 5bI. G. Stará, I. Stary, M. Tichy, J. Závada, P. Fiedler, J. Org. Chem. 1994, 59, 1326;
- 5cA.-H. Li, L.-X. Dai, X.-L. Hou, Y.-Z. Huang, F.-W. Li, J. Org. Chem. 1996, 61, 489;
- 5dA.-H. Li, Y.-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia, L. Lin, Angew. Chem. Int. Ed. Engl. 1997, 36, 1317; Angew. Chem. 1997, 109, 1375;
- 5eK. Julienne, P. Metzner, J. Org. Chem. 1998, 63, 4532;
- 5fA. Solladié-Cavallo, L. Bouérat, M. Roje, Tetrahedron Lett. 2000, 41, 7309;
- 5gA. Solladié-Cavallo, M. Roje, T. Isarno, V. Sunjic, V. Vinkovic, Eur. J. Org. Chem. 2000, 1077;
- 5hS. Ye, Z.-Z. Huang, C.-A. Xia, Y. Tang, L.-X. Dai, J. Am. Chem. Soc. 2002, 124, 2432;
- 5iY. Miyake, A. Oyamada, Y. Nishibayashi, S. Uemura, Heteroat. Chem. 2002, 13, 270;
- 5jV. K. Aggarwal, I. Bae, H.-Y. Lee, J. Richardson, D. T. Williams, Angew. Chem. Int. Ed. 2003, 42, 3274; Angew. Chem. 2003, 115, 3396;
- 5kV. K. Aggarwal, G. Y. Fang, A. T. Schmidt, J. Am. Chem. Soc. 2005, 127, 1642;
- 5lM. Davoust, J.-F. Brière, P.-A. Jaffrès, P. Metzner, J. Org. Chem. 2005, 70, 4166;
- 5mV. K. Aggarwal, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. Robiette, C. Smith, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105;
- 5nM. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. Int. Ed. 2006, 45, 7066; Angew. Chem. 2006, 118, 7224;
- 5oX.-M. Deng, P. Cai, S. Ye, X.-L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.-D. Wu, L.-X. Dai, J. Am. Chem. Soc. 2006, 128, 9730;
- 5pE. L. Myers, J. G. de Vries, V. K. Aggarwal, Angew. Chem. Int. Ed. 2007, 46, 1893; Angew. Chem. 2007, 119, 1925;
- 5qG. Y. Fang, O. A. Wallner, N. D. Blasio, X. Ginesta, J. N. Harvey, V. K. Aggarwal, J. Am. Chem. Soc. 2007, 129, 14632;
- 5rM. Hansch, O. Illa, E. M. McGarrigle, V. K. Aggarwal, Chem. Asian J. 2008, 3, 1657;
- 5sL.-Q. Lu, J.-J. Zhang, F. Li, Y. Cheng, J. An, J.-R. Chen, W.-J. Xiao, Angew. Chem. Int. Ed. 2010, 49, 4495; Angew. Chem. 2010, 122, 4597;
- 5tM. Arshad, M. A. Fernández, E. M. McGarrigle, V. K. Aggarwal, Tetrahedron: Asymmetry 2010, 21, 1771;
- 5uO. Illa, M. Arshad, A. Ros, E. M. McGarrigle, V. K. Aggarwal, J. Am. Chem. Soc. 2010, 132, 1828;
- 5vF. Sarabia, C. Vivar-García, M. García-Castro, C. García-Ruiz, F. Martín-Gálvez, A. Sánchez-Ruiz, S. Chammaa, Chem. Eur. J. 2012, 18, 15190;
- 5wS. P. Fritz, Z. Ali, M. G. Unthank, E. M. McGarrigle, V. K. Aggarwal, Helv. Chim. Acta 2012, 95, 2384;
- 5xO. Illa, M. Namutebi, C. Saha, M. Ostovar, C. C. Chen, M. F. Haddow, S. Nocquet-Thibault, M. Lusi, E. M. McGarrigle, V. K. Aggarwal, J. Am. Chem. Soc. 2013, 135, 11951;
- 5yX.-Z. Zhang, J.-Y. Du, Y.-H. Deng, W.-D. Chu, X. Yan, K.-Y. Yu, C.-A. Fan, J. Org. Chem. 2016, 81, 2598.
- 6J.-P. Cheng, B. Liu, X.-M. Zhang, J. Org. Chem. 1998, 63, 7574.
- 7
- 7aR. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 16620;
- 7bL. Wang, S. Shirakawa, K. Maruoka, Angew. Chem. Int. Ed. 2011, 50, 5327; Angew. Chem. 2011, 123, 5439;
- 7cS. Shirakawa, S. J. Terao, R. He, K. Maruoka, Chem. Commun. 2011, 47, 10557;
- 7dS. Shirakawa, K. Ota, S. J. Terao, K. Maruoka, Org. Biomol. Chem. 2012, 10, 5753;
- 7eS. Shirakawa, L. Wang, A. Kasai, K. Maruoka, Chem. Eur. J. 2012, 18, 8588;
- 7fS. Shirakawa, A. Kasai, T. Tokuda, K. Maruoka, Chem. Sci. 2013, 4, 2248;
- 7gS. Shirakawa, T. Tokuda, A. Kasai, K. Maruoka, Org. Lett. 2013, 15, 3350;
- 7hS. Shirakawa, L. Wang, R. He, S. Arimitsu, K. Maruoka, Chem. Asian J. 2014, 9, 1586;
- 7iS. Shirakawa, K. Maruoka, Tetrahedron Lett. 2014, 55, 3833;
- 7jS. P. Bew, G. R. Stephenson, J. Rouden, P.-A. Ashford, M. Bourane, A. Charvet, V. M. D. Dalstein, R. Jauseau, G. D. Hiatt-Gipson, L. A. Martinez-Lozano, Adv. Synth. Catal. 2015, 357, 1245.
- 8Fan et al. examined an asymmetric conjugate addition catalyzed by a chiral tertiary sulfonium salt under ordinary phase-transfer conditions using Cs2CO3 as a base, but the product was obtained in 0 % ee; see: X.-Z. Zhang, Y.-H. Deng, X. Yan, K.-Y. Yu, F.-X. Wang, X.-Y. Ma, C.-A. Fan, J. Org. Chem. 2016, 81, 5655.
- 9
- 9aY.-H. Liao, X.-L. Liu, Z.-J. Wu, L.-F. Cun, X.-M. Zhang, W.-C. Yuan, Org. Lett. 2010, 12, 2896;
- 9bL. Li, W. Chen, W. Yang, Y. Pan, H. Liu, C.-H. Tan, Z. Jiang, Chem. Commun. 2012, 48, 5124;
- 9cX. Yang, C. Wang, Q. Ni, D. Enders, Synthesis 2012, 2601;
- 9dJ. Zhou, L.-N. Jia, L. Peng, Q.-L. Wang, F. Tian, X.-Y. Xu, L.-X. Wang, Tetrahedron 2014, 70, 3478;
- 9eS. Shirakawa, H. Makino, T. Yoshidome, K. Maruoka, Tetrahedron 2014, 70, 7128.
- 10For examples of chiral bifunctional quaternary ammonium and phosphonium salts with a urea group, see:
- 10aP. Bernal, R. Fernández, J. M. Lassaletta, Chem. Eur. J. 2010, 16, 7714;
- 10bK. M. Johnson, M. S. Rattley, F. Sladojevich, D. M. Barber, M. G. Nuñez, A. M. Goldys, D. J. Dixon, Org. Lett. 2012, 14, 2492;
- 10cD. Cao, Z. Chai, J. Zhang, Z. Ye, H. Xiao, H. Wang, J. Chen, X. Wu, G. Zhao, Chem. Commun. 2013, 49, 5972;
- 10dM. Li, P. A. Woods, M. D. Smith, Chem. Sci. 2013, 4, 2907;
- 10eH.-Y. Wang, Z. Chai, G. Zhao, Tetrahedron 2013, 69, 5104;
- 10fD. Cao, J. Zhang, H. Wang, G. Zhao, Chem. Eur. J. 2015, 21, 9998;
- 10gM. Tiffner, J. Novacek, A. Busillo, K. Gratzer, A. Massa, M. Waser, RSC Adv. 2015, 5, 78941.
- 11Remaining starting materials 4 a and 5 a were observed after the reaction.
- 12Longer reaction times did not improve the yield.
- 13The effect of the amount of water was also examined (Scheme S1).
- 14
- 14aS. Kaneko, Y. Kumatabara, S. Shimizu, K. Maruoka, S. Shirakawa, Chem. Commun. 2017, 53, 119; see also:
- 14bS. Shirakawa, S. Liu, S. Kaneko, Y. Kumatabara, A. Fukuda, Y. Omagari, K. Maruoka, Angew. Chem. Int. Ed. 2015, 54, 15767; Angew. Chem. 2015, 127, 15993;
- 14cY. Kumatabara, S. Kaneko, S. Nakata, S. Shirakawa, K. Maruoka, Chem. Asian J. 2016, 11, 2126.
- 15
- 15aT. Ohshima, T. Shibuguchi, Y. Fukuta, M. Shibasaki, Tetrahedron 2004, 60, 7743;
- 15bT. Kamachi, K. Yoshizawa, Org. Lett. 2014, 16, 472;
- 15cC. P. Johnston, A. Kothari, T. Sergeieva, S. I. Okovytyy, K. E. Jackson, R. S. Paton, M. D. Smith, Nat. Chem. 2015, 7, 171;
- 15dQ. Peng, R. S. Paton, Acc. Chem. Res. 2016, 49, 1042;
- 15eJ. Novacek, J. A. Izzo, M. J. Vetticatt, M. Waser, Chem. Eur. J. 2016, 22, 17339.
- 16Reactions on larger scale (x10, 0.70 mmol) gave similar results (Scheme S2).
