A Highly Efficient and Enantioselective Access to Tetrahydroisoquinoline Alkaloids: Asymmetric Hydrogenation with an Iridium Catalyst†
Mingxin Chang
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Search for more papers by this authorWei Li
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Search for more papers by this authorCorresponding Author
Prof. Xumu Zhang
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/Search for more papers by this authorMingxin Chang
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Search for more papers by this authorWei Li
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Search for more papers by this authorCorresponding Author
Prof. Xumu Zhang
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/
Department of Chemistry and Chemical Biology and Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://chem.rutgers.edu/∼xumuweb/Search for more papers by this authorThis research was supported by the National Institutes of Health (GM58832). We thank Dr. Furong Sun for HRMS analysis.
Graphical Abstract
Effizient und enantioselektiv: Mit dem dimeren, iodverbrückten Iridiumkomplex [{Ir(H)[(S,S)-(f)-binaphan]}2(μ-I)3]+I− (1) konnte eine Vielzahl an Tetrahydroisochinolin-Alkaloiden, darunter auch die Teilstruktur des Wirkstoffs Solifenacin, mit ausgezeichneter Enantioselektivität und hoher Umsatzzahl hergestellt werden (siehe Schema).
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References
- 1
- 1aR. Paul, J. A. Coppola, E. Cohen, J. Med. Chem. 1972, 15, 720;
- 1b The Chemistry and Biology of Isoquinoline Alkaloids (Eds.: ), Springer, Berlin, 1985;
- 1cD. Jack, R. Williams, Chem. Rev. 2002, 102, 1669;
- 1dP. M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, Wiley, Chichester, 2002, p. 315;
- 1eK. W. Bentley, Nat. Prod. Rep. 2006, 23, 444;
- 1fM. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341.
- 2aA. Brossi, S. Teitel, Helv. Chim. Acta 1971, 54, 1564;
- 2bH. M. Kothari, M. G. Dave, B. Pandey, Patent WO 2011048607, 2011.
- 3
- 3aD. Taniyama, M. Hasegawa, K. Tomioka, Tetrahedron: Asymmetry 1999, 10, 221;
- 3bK. T. Wanner, H. Beerb, G. Hofnera, M. Ludwig, Eur. J. Org. Chem. 1998, 2019;
10.1002/(SICI)1099-0690(199809)1998:9<2019::AID-EJOC2019>3.0.CO;2-T CAS Web of Science® Google Scholar
- 3cK. Kurihara, Y. Yamamoto, N. Miyauraa, Adv. Synth. Catal. 2009, 351, 260;
- 3dK. Umetsu, N. Asao, Tetrahedron Lett. 2008, 49, 2722;
- 3eS. Wang, M. B. Onaran, C. T. Seto, Org. Lett. 2010, 12, 2690;
- 3fF. Louafi, J.-P. Hurvois, A. Chibani, T. Roisnel, J. Org. Chem. 2010, 75, 5721;
- 3gM. Amat, V. Elias, N. Llor, F. Subrizi, E. Molins, J. Bosch, Eur. J. Org. Chem. 2010, 4017.
- 4T. Ohkuma, M. Kitamura, R. Noyori in Catalytic Asymmetric Synthesis, 2nd ed. ), Wiley, New York, 2000, p. 1.
10.1002/0471721506.ch1 Google Scholar
- 5
- 5aC. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8952;
- 5bT. Morimoto, K. Achiwa, Tetrahedron: Asymmetry 1995, 6, 2661;
- 5cT. Morimoto, N. Suzuki, K. Achiwa, Heterocycles 1996, 43, 2557;
- 5dG. Zhu, X. Zhang, Tetrahedron: Asymmetry 1998, 9, 2415;
- 5eC. J. Cobley, J. P. Henschke, Adv. Synth. Catal. 2003, 345, 195;
- 5fE. Guiu, C. Claver, J. Benet-Buchholz, S. Castillon, Tetrahedron: Asymmetry 2004, 15, 3365;
- 5gM. Jackson, I. C. Lennon, Tetrahedron Lett. 2007, 48, 1831;
- 5hC. Li, J. Xiao, J. Am. Chem. Soc. 2008, 130, 13208.
- 6
- 6aN. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916;
- 6bE. Vedejs, P. Trapencieris, E. Suna, J. Org. Chem. 1999, 64, 6724;
- 6cJ. Mao, D. C. Baker, Org. Lett. 1999, 1, 841;
- 6dP. Roszkowski, K. Wojtasiewicz, A. Leniewski, J. K. Maurin, T. Lis, Z. Czarnocki, J. Mol. Catal. A 2005, 232, 143;
- 6eJ. Wu, F. Wang, Y. Ma, X. Cui, L. Cun, J. Zhu, J. Deng, B. Yu, Chem. Commun. 2006, 1766;
- 6fJ. Canivet, G. Süss-Fink, Green Chem. 2007, 9, 391;
- 6gD. S. Matharu, J. E. D. Martins, M. Wills, Chem. Asian J. 2008, 3, 1374;
- 6hJ. E. D. Martins, G. J. Clarkson, M. Wills, Org. Lett. 2009, 11, 847;
- 6iL. Evanno, J. Ormala, P. M. Pihko, Chem. Eur. J. 2009, 15, 12963;
- 6jJ. E. D. Martins, M. A. C. Redondo, M. Wills, Tetrahedron: Asymmetry 2010, 21, 2258.
- 7Y. Ishii, K. Takaoka, M. Inakoshi, S. Nakagawa, K. Nagata, N. Yorimoto, M. Takeuchi, Y. Yonetoku, Patent WO 2005075474A1, 2005.
- 8
- 8aD. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533;
Angew. Chem. Int. Ed. 2001, 40, 3425;
10.1002/1521-3773(20010917)40:18<3425::AID-ANIE3425>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- 8bG. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. O’Shea, C.-Y. Chen, I. W. Davies, X. Zhang, J. Am. Chem. Soc. 2009, 131, 9882;
- 8cG. Hou, W. Li, M. Ma, X. Zhang, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12844;
- 8dM. Chang, W. Li, G. Hou, X. Zhang, Adv. Synth. Catal. 2010, 352, 3121.
- 9
- 9aF. Spindler, H.-U. Blaser in Handbook of Homogeneous Hydrogenation, Vol. 3 (Eds.: ), Wiley-VCH, Weinheim, 2007, pp. 1193;
- 9bJ.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713.
- 10Y. Chi, Y.-G. Zhou, X. Zhang, J. Org. Chem. 2003, 68, 4120.
- 11For reviews, see:
- 11aK. Fagnou, M. Lautens, Angew. Chem. 2002, 114, 26;
10.1002/1521-3757(20020104)114:1<26::AID-ANGE26>3.0.CO;2-O Google ScholarAngew. Chem. Int. Ed. 2002, 41, 26;
- 11bE. M. Vogl, H. Groeger, M. Shibasaki, Angew. Chem. 1999, 111, 1672;
10.1002/(SICI)1521-3757(19990601)111:11<1672::AID-ANGE1672>3.0.CO;2-2 Google ScholarAngew. Chem. Int. Ed. 1999, 38, 1570;10.1002/(SICI)1521-3773(19990601)38:11<1570::AID-ANIE1570>3.0.CO;2-Y CAS PubMed Web of Science® Google Scholar
- 11cD. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159;
10.1002/ange.19951071004 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 1059.
- 12T. Yamagata, H. Tadaoka, M. Nagata, T. Hirao, Y. Kataoka, V. Ratovelomanana-Vidal, J. P. Genet, K. Mashima, Organometallics 2006, 25, 2505.
- 13
- 13aM. Movassaghi, M. D. Hill, Org. Lett. 2008, 10, 3485;
- 13bJ. M. Joo, R. A. David, Y. Yuan, C. Lee, Org. Lett. 2010, 12, 5704.
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