Exploiting Distal Reactivity of Coumarins: A Rhodium-Catalyzed Vinylogous Asymmetric Ring-Opening Reaction
Dr. Charles C. J. Loh
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorMatthias Schmid
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorBrendan Peters
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorDr. Xiang Fang
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorDr. Charles C. J. Loh
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorMatthias Schmid
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorBrendan Peters
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorDr. Xiang Fang
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada
Search for more papers by this authorAbstract
While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning γ-reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium-catalyzed asymmetric ring-opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.
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References
- 1
- 1aR. C. Fuson, Chem. Rev. 1935, 16, 1–27;
- 1bG. Casiraghi, F. Zanardi, Chem. Rev. 2000, 100, 1929–1972;
- 1cS. E. Denmark, J. R. Heemstra, Jr., G. L. Beutner, Angew. Chem. Int. Ed. 2005, 44, 4682–4698; Angew. Chem. 2005, 117, 4760–4777;
- 1dG. Casiraghi, F. Zanardi, L. Battistini, G. Rassu, Synlett 2009, 1525–1542;
- 1eH.-L. Cui, Y.-C. Chen, Chem. Commun. 2009, 4479–4486;
- 1fG. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076–3154;
- 1gC. Schneider, F. Abels, Org. Biomol. Chem. 2014, 12, 3531–3543.
- 2For selected recent examples:
- 2aB. Ranieri, A. Sartori, C. Curti, L. Battistini, G. Rassu, G. Pelosi, G. Casiraghi, F. Zanardi, Org. Lett. 2014, 16, 932–935;
- 2bS. Basu, V. Gupta, J. Nickel, C. Schneider, Org. Lett. 2014, 16, 274–277;
- 2cG. Zhan, Q. He, X. Yuan, Y.-C. Chen, Org. Lett. 2014, 16, 6000–6003;
- 2dY. Gu, Y. Wang, T.-Y. Yu, Y.-M. Liang, P.-F. Xu, Angew. Chem. Int. Ed. 2014, 53, 14128–14131; Angew. Chem. 2014, 126, 14352–14355;
- 2eQ. Wang, M. van Gemmeren, B. List, Angew. Chem. Int. Ed. 2014, 53, 13592–13595; Angew. Chem. 2014, 126, 13810–13813;
- 2fX. Tian, N. Hofmann, P. Melchiorre, Angew. Chem. Int. Ed. 2014, 53, 2997–3000; Angew. Chem. 2014, 126, 3041–3044;
- 2gL. Yin, H. Takada, S. Lin, N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2014, 53, 5327–5331; Angew. Chem. 2014, 126, 5431–5435;
- 2hN. Di Iorio, P. Righi, A. Mazzanti, M. Mancinelli, A. Ciogli, G. Bencivenni, J. Am. Chem. Soc. 2014, 136, 10250–10253;
- 2iL. Dell'Amico, G. Rassu, V. Zambrano, A. Sartori, C. Curti, L. Battistini, G. Pelosi, G. Casiraghi, F. Zanardi, J. Am. Chem. Soc. 2014, 136, 11107–11114;
- 2jX. Xiao, H. Mei, Q. Chen, X. Zhao, L. Lin, X. Liu, X. Feng, Chem. Commun. 2015, 51, 580–583;
- 2kJ. Li, R. Huang, Y.-K. Xing, G. Qiu, H.-Y. Tao, C.-J. Wang, J. Am. Chem. Soc. 2015, 137, 10124–10127.
- 3For a review and selected recent total syntheses utilizing vinylogy, see:
- 3aM. Kalesse, M. Cordes, G. Symkenberg, H.-H. Lu, Nat. Prod. Rep. 2014, 31, 563–594;
- 3bM. T. Gieseler, M. Kalesse, Org. Lett. 2014, 16, 548–551;
- 3cJ. Li, P. Yang, M. Yao, J. Deng, A. Li, J. Am. Chem. Soc. 2014, 136, 16477–16480;
- 3dH. Fuwa, T. Muto, K. Sekine, M. Sasaki, Chem. Eur. J. 2014, 20, 1848–1860;
- 3eS. Pan, J. Xuan, B. Gao, A. Zhu, H. Ding, Angew. Chem. Int. Ed. 2015, 54, 6905–6908; Angew. Chem. 2015, 127, 7009–7012.
- 4R. Jana, J. J. Partridge, J. A. Tunge, Angew. Chem. Int. Ed. 2011, 50, 5157–5161; Angew. Chem. 2011, 123, 5263–5267.
- 5M. Chen, J. F. Hartwig, Angew. Chem. Int. Ed. 2014, 53, 12172–12176; Angew. Chem. 2014, 126, 12368–12372.
- 6L. Næsborg, K. S. Halskov, F. Tur, S. M. N. Mønsted, K. A. Jørgensen, Angew. Chem. Int. Ed. 2015, 54, 10193–10197; Angew. Chem. 2015, 127, 10331–10335.
- 7M. Ikeda, Y. Miyake, Y. Nishibayashi, Organometallics 2012, 31, 3810–3813.
- 8I. S. Makarov, T. Kuwahara, X. Jusseau, I. Ryu, A. T. Lindhardt, T. Skrydstrup, J. Am. Chem. Soc. 2015, 137, 14043–14046.
- 9
- 9aA. M. Hyde, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 177–180; Angew. Chem. 2008, 120, 183–186;
- 9bD. S. Huang, J. F. Hartwig, Angew. Chem. Int. Ed. 2010, 49, 5757–5761; Angew. Chem. 2010, 122, 5893–5897; for other recent reports, see:
- 9cF. Wagner, K. Harms, U. Koert, Org. Lett. 2015, 17, 5670–5673;
- 9dM. Grigalunas, P.-O. Norrby, O. Wiest, P. Helquist, Angew. Chem. Int. Ed. 2015, 54, 11822–11825; Angew. Chem. 2015, 127, 11988–11991.
- 10
- 10aJ. R. S. Hoult, M. Payá, Gen. Pharmacol. 1996, 27, 713–722;
- 10bA. Estévez-Braun, A. G. González, Nat. Prod. Rep. 1997, 14, 465–475;
- 10cS. R. Trenor, A. R. Shultz, B. J. Love, T. E. Long, Chem. Rev. 2004, 104, 3059–3077;
- 10dK. N. Venugopala, V. Rashmi, B. Odhav, BioMed Res. Int. 2013, 2013, 1–14. For selected examples of bioactive coumarins, see:
- 10eC. Ito, M. Itoigawa, Y. Mishina, V. C. Filho, F. Enjo, H. Tokuda, H. Nishino, H. Furukawa, J. Nat. Prod. 2003, 66, 368–371;
- 10fB. Ngameni, M. Touaibia, R. Patnam, A. Belkaid, P. Sonna, B. T. Ngadjui, B. Annabi, R. Roy, Phytochemistry 2006, 67, 2573–2579;
- 10gH. Yang, B. Jiang, K. A. Reynertson, M. J. Basile, E. J. Kennelly, J. Agric. Food Chem. 2006, 54, 4114–4120;
- 10hK. Chun, S.-K. Park, H. M. Kim, Y. Choi, M.-H. Kim, C.-H. Park, B.-Y. Joe, T. G. Chun, H.-M. Choi, H.-Y. Lee, S. H. Hong, M. S. Kim, K.-Y. Nam, G. Han, Bioorg. Med. Chem. 2008, 16, 530–535.
- 11X. Huang, Y.-H. Wen, F.-T. Zhou, C. Chen, D.-C. Xu, J.-W. Xie, Tetrahedron Lett. 2010, 51, 6637–6640.
- 12
- 12aM. Lautens, K. Fagnou, T. Rovis, J. Am. Chem. Soc. 2000, 122, 5650–5651;
- 12bM. Lautens, K. Fagnou, J. Am. Chem. Soc. 2001, 123, 7170–7171;
- 12cR. Webster, C. Böing, M. Lautens, J. Am. Chem. Soc. 2009, 131, 444–445;
- 12dJ. Zhu, G. C. Tsui, M. Lautens, Angew. Chem. Int. Ed. 2012, 51, 12353–12356; Angew. Chem. 2012, 124, 12519–12522;
- 12eL. Zhang, C. M. Le, M. Lautens, Angew. Chem. Int. Ed. 2014, 53, 5951–5954; Angew. Chem. 2014, 126, 6061–6064;
- 12fC. C. J. Loh, X. Fang, B. Peters, M. Lautens, Chem. Eur. J. 2015, 21, 13883–13887.
- 13For selected reports in ARO reactions catalyzed by other metals, see:
- 13aM. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804–1805;
- 13bD. K. Rayabarapu, C.-F. Chiou, C.-H. Cheng, Org. Lett. 2002, 4, 1679–1682;
- 13cF. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703–2705;
- 13dK. Villeneuve, W. Tam, J. Am. Chem. Soc. 2006, 128, 3514–3515;
- 13eK. Villeneuve, W. Tam, Eur. J. Org. Chem. 2006, 5449–5453;
- 13fA. Tenaglia, S. Marc, J. Org. Chem. 2006, 71, 3569–3575;
- 13gA. Tenaglia, S. Marc, L. Giordano, I. De Riggi, Angew. Chem. Int. Ed. 2011, 50, 9062–9065; Angew. Chem. 2011, 123, 9228–9231;
- 13hH. Cheng, D. Yang, J. Org. Chem. 2012, 77, 9756–9765;
- 13iL. Meng, W. Yang, X. Pan, M. Tao, G. Cheng, S. Wang, H. Zeng, Y. Long, D. Yang, J. Org. Chem. 2015, 80, 2503–2512.
- 14CCDC 1446936 (3 k), 1446937 (3 r), and 1446938 (3 u) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
- 15We also attempted a highly sterically hindered substrate bearing a phenyl group on the γ-position (see the Supporting Information). While extensive decomposition was observed in a complex mixture, we still managed to isolate and characterize one of the diastereomers with 28 % yield and 96 % ee, thus further augmenting the tolerance of our protocol towards γ-sterically hindered cyanocoumarins.
- 16For an example of rhodium-catalyzed decarboxylation, see: C. Li, B. Breit, J. Am. Chem. Soc. 2014, 136, 862–865.
- 17A. M. Breckenridge, S. Cholerton, J. A. D. Hart, B. K. Park, A. K. Scott, Br. J. Pharmacol. 1985, 84, 81–91.
- 18P. S. Fogue, P. K. Lunga, E. S. Fondjo, J. D. D. Tamokou, B. Thaddée, J. Tsemeugne, A. T. Tchapi, J.-R. Kuiate, Mycoses 2012, 55, 310–317.
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