One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines
Huan Zhou
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorYuan Liu
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorSuhua Yang
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorProf. Dr. Le Zhou
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mingxin Chang
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorHuan Zhou
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorYuan Liu
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorSuhua Yang
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorProf. Dr. Le Zhou
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mingxin Chang
Department of Chemistry and Chemical Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi, 712100 PR China
Search for more papers by this authorAbstract
A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.
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 |
|---|---|
| ange201611181-sup-0001-misc_information.pdf3.3 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
- 1
- 1a The Chemistry and Biology of Isoquinoline Alkaloids (Eds.: ), Springer, Berlin, 1985;
- 1bP. M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, Wiley, Chichester, 2002, p. 315;
- 1cK. W. Bentley, Nat. Prod. Rep. 2006, 23, 444.
- 2
- 2aA. Brossi, S. Teitel, Helv. Chim. Acta 1971, 54, 1564;
- 2bL. Y. Luk, S. Bunn, D. K. Liscombe, P. J. Facchini, M. E. Tanner, Biochemistry 2007, 46, 10153;
- 2cR. Gitto, M. L. Barreca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, A. Chimirri, J. Med. Chem. 2003, 46, 197;
- 2dA. M. Bechter, Anesth. Analg. 1977, 56, 305;
- 2eT. Weller, R. Koberstein, H. Aissaoui, M. Clozel, W. Fischli, WO 2005/118548, 2005;
- 2fH. M. Kothari, M. G. Dave, B. Pandey, WO 2011048607, 2011.
- 3
- 3aM. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341;
- 3bJ. Stöckigt, A. P. Antonchick, F. Wu, H. Waldmann, Angew. Chem. Int. Ed. 2011, 50, 8538; Angew. Chem. 2011, 123, 8692;
- 3cM. Chrzanowska, A. Grajewska, M. D. Rozwadowska, Chem. Rev. 2016, 116, 12369.
- 4For reviews and selected recent results, see:
- 4aG. Shang, W. Li, X. Zhang in Catalytic Asymmetric Synthesis, 3rd ed. ), Wiley, New York, 2010, pp. 343;
- 4bJ.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713;
- 4cM. Chang, W. Li, X. Zhang, Angew. Chem. Int. Ed. 2011, 50, 10679; Angew. Chem. 2011, 123, 10867;
- 4dF. Berhal, Z. Wu, Z. G. Zhang, T. Ayad, V. Ratovelomanana-Vidal, Org. Lett. 2012, 14, 3308;
- 4eJ.-H. Xie, P.-C. Yan, Q.-Q. Zhang, K.-X. Yuan, Q.-L. Zhou, ACS Catal. 2012, 2, 561;
- 4fZ. Wu, M. Perez, M. Scalone, T. Ayad, V. Ratovelomanana-Vidal, Angew. Chem. Int. Ed. 2013, 52, 4925; Angew. Chem. 2013, 125, 5025;
- 4gY. Ji, L. Shi, M.-W. Chen, G.-S. Feng, Y.-G. Zhou, J. Am. Chem. Soc. 2015, 137, 10496;
- 4hF. Chen, A.-E. Surkus, L. He, M.-M. Pohl, J. Radnik, C. Topf, K. Junge, M. Beller, J. Am. Chem. Soc. 2015, 137, 11718;
- 4iA. Karakulina, A. Gopakumar, I. Akcok, B. L. Roulier, T. LaGrange, S. A. Katsyuba, S. Das, P. J. Dyson, Angew. Chem. Int. Ed. 2016, 55, 292; Angew. Chem. 2016, 128, 300.
- 5
- 5aT. Ohkuma, M. Kitamura, R. Noyori in Catalytic Asymmetric Synthesis, 2nd ed. ), Wiley-VCH, New York, 2000, chap. 1, pp. 1–110;
10.1002/0471721506.ch1 Google Scholar
- 5bB. Alberts, D. Bray, J. Lewis, M. Raff, K. Roberts, J. D. Watson, Molecular Biology of the Cell, Garland, New York, 2002;
- 5cT. Ohkuma, R. Noyori in Comprehensive Asymmetric Catalysis, Suppl. 1 (Eds.: ), Springer, New York, 2004;
- 5dM. Kitamura, R. Noyori, in Ruthenium in Organic Synthesis (Ed: ), Wiley-VCH, Weinheim, 2004, p. 3;
10.1002/3527603832.ch2 Google Scholar
- 5eS. Warren, P. Wyatt in Organic Synthesis: The Disconnection Approach, 2nd ed., Wiley, Oxford, 2008, p. 54;
- 5fC. Claver, E. Fernández in Modern Reduction Methods (Eds.: ), Wiley-VCH, Weinheim, 2008, chap. 10, p. 237;
M. Wills in Modern Reduction Methods (Eds.: ), Wiley-VCH, Weinheim 2008, chap. 11, p. 271.
10.1002/9783527622115.ch11 Google Scholar
- 6H.-U. Blaser, H.-P. Buser, H.-P. Jalett, B. Pugin, F. Spindler, Synlett 1999, 867.
- 7
- 7aT. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753;
- 7bC. Wang, J. Xiao, Top. Curr. Chem. 2014, 343, 261.
- 8
- 8aG. D. Williams, R. A. Pike, C. E. Wade, M. Wills, Org. Lett. 2003, 5, 4227;
- 8bN. A. Strotman, C. A. Baxter, K. M. J. Brands, E. Cleator, S. W. Krska, R. A. Reamer, D. J. Wallace, T. J. Wright, J. Am. Chem. Soc. 2011, 133, 8362.
- 9F. Spindler, H.-U. Blaser in Handbook of Homogeneous Hydrogenation, Vol. 3 (Eds.: ), Wiley-VCH, Weinheim, 2007, pp. 1193.
- 10For reviews of additive effects and selected examples in asymmetric reductive amination, see:
- 10aL. Hong, W. Sun, D. Yang, G. Li, R. Wang, Chem. Rev. 2016, 116, 4006;
- 10bC. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967;
- 10cM. Chang, S. Liu, X. Zhang, Org. Lett. 2013, 15, 4354;
- 10dH. Huang, X. Liu, L. Zhou, M. Chang, X. Zhang, Angew. Chem. Int. Ed. 2016, 55, 5309; Angew. Chem. 2016, 128, 5395.
- 11
- 11aH. Tadaoka, D. Cartigny, T. Nagano, T. Gosavi, T. Ayad, J.-P. Genêt, T. Ohshima, V. Ratovelomanana-Vidal, K. Mashima, Chem. Eur. J. 2009, 15, 9990;
- 11bJ.-P. Genet, T. Ayad, V. Ratovelomanana-Vidal, Chem. Rev. 2014, 114, 2824.
- 12T. Yamagata, H. Tadaoka, M. Nagata, T. Hirao, Y. Kataoka, V. Ratovelomanana-Vidal, J. P. Genet, K. Mashima, Organometallics 2006, 25, 2505.
- 13M. Chang, W. Li, G. Hou, X. Zhang, Adv. Synth. Catal. 2010, 352, 3121.
- 14
- 14aR. Naito, Y. Yonetoku, Y. Okamoto, A. Toyoshima, K. Ikeda, M. J. Takeuchi, J. Med. Chem. 2005, 48, 6597;
- 14bZ.-S. Ye, R.-N. Guo, X.-F. Cai, M.-W. Chen, L. Shi, Y.-G. Zhou, Angew. Chem. Int. Ed. 2013, 52, 3685; Angew. Chem. 2013, 125, 3773;
- 14cG. N. Trinadhachari, A. G. Kamat, B. V. Balaji, K. J. Prabahar, K. M. Naidu, K. R. Babu, P. D. Sanasi, Org. Process Res. Dev. 2014, 18, 934.
- 15
- 15aM. Ohkubo, A. Kuno, K. Katsuta, Y. Ueda, K. Shirakawa, H. Nakanishi, I. Nakanishi, T. Kinoshita, H. Takasugi, Chem. Pharm. Bull. 1996, 44, 95;
- 15bX. Li, I. Coldham, J. Am. Chem. Soc. 2014, 136, 5551;
- 15cM. Ludwig, C. E. Hoesl, G. Höfner, K. T. Wanner, Eur. J. Med. Chem. 2006, 41, 1003.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
