An Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3′-F2-BINOL

Journal of Organic Chemistry

Volumn 81, Issue 6, 2016, Pages 2665-2669

  Zhang, Yongda ^a   Wu, Jiang Ping ^a   Li, Guisheng ^a   Fandrick, Keith R ^a   Gao, Joe ^a   Tan, Zhulin ^a   Johnson, Joe ^a   Li, Wenjie ^a   Sanyal, Sanjit ^a   Wang, Jun ^a   Sun, Xiufeng ^a   Lorenz, Jon C ^a   Rodriguez, Sonia ^a   Reeves, Jonathan T ^a   Grinberg, Nelu ^a   Lee, Heewon ^a   Yee, Nathan ^a   Lu, Bruce Z ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE; 3,3'-F2-BINOL; 3-CHLORO-1-PHENYLPROPAN-1-ONE; KETONE; NAPHTHOL DERIVATIVE; PROPANE;

ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

11-BETA-HYDROXYSTEROID DEHYDROGENASES; CATALYSIS; KETONES; NAPHTHOLS; PROPANE; STEREOISOMERISM;

EID: 84961779064     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b00189     Document Type: Article

References (31)

1. Wamil, M.; Seckl, J. R. Drug Discovery Today 2007, 12, 504 10.1016/j.drudis.2007.06.001
2. Blum, A.; Raum, A.; Maser, E. Biochemistry 2003, 42, 4108 10.1021/bi027425d
3. Becker, C. L.; Engstrom, K. M.; Kerdesky, F. A.; Tolle, J. C.; Wagaw, S. H.; Wang, W. Org. Process Res. Dev. 2008, 12, 1114 10.1021/op800065q
4. Zhang, Y.; Li, N.; Qu, B.; Ma, S.; Lee, H.; Gonnella, N. C.; Gao, J.; Li, W.; Tan, Z.; Reeves, J. T.; Wang, J.; Lorenz, J. C.; Li, G.; Reeves, D. C.; Premasiri, A. P.; Grinberg, N. G.; Haddad, N.; Lu, B. Z.; Song, J. J.; Senanayake, C. H. Org. Lett. 2013, 15, 1710 10.1021/ol400498a
5. Hatano, M.; Ishihara, K. Synthesis 2008, 11, 1647 10.1055/s-2008-1067046
6. Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774 10.1021/cr1004474
7. Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367 10.1021/ar800170y
8. For the asymmetric methallylation of ketones, see: Román, J. G.; Soderquist, J. A. J. Org. Chem. 2007, 72, 9772 10.1021/jo701633k
9. Kim, J. G.; Camp, E. H.; Walsh, P. J. Org. Lett. 2006, 8, 4413 10.1021/ol061417y
10. Miller, J. J.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 2752 10.1021/ja068915m
11. For example, the reaction gave 13% conversion with 3:1 er overnight when methallyl siloxane was applied for the asymmetric allylation of 7 under the conditions for allylation: [(R)-DIFLUORPHOS (5 mol %), AgF (5 mol %), MeOH (1 equiv), and THF from -78 to 23 °C]. See: Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556 10.1021/ja0553351
12. Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910 10.1021/ja047200l
13. Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660 10.1021/ja0651308
14. Barnett, D. S.; Moquist, P. N.; Schaus, S. E. Angew. Chem., Int. Ed. Eng. 2009, 48, 8679
15. Cook, G. R.; Kargbo, R.; Maity, B. Org. Lett. 2005, 7, 2767 10.1021/ol051160o
16. Kargbo, R.; Takahashi, Y.; Bhor, S.; Cook, G. R.; Lloyd-Jones, G. C.; Shepperson, I. R. J. Am. Chem. Soc. 2007, 129, 3846 10.1021/ja070742t
17. Orito, Y.; Hashimoto, S.; Ishizuka, T.; Nakajima, M. Tetrahedron 2006, 62, 390 10.1016/j.tet.2005.09.074
18. Turner, H. M.; Patel, J.; Niljianskul, N.; Chong, J. M. Org. Lett. 2011, 13, 5796 10.1021/ol202391r
19. Ichibakase, T.; Kaneko, T.; Orito, Y.; Kotani, S.; Nakajima, M. Tetrahedron 2012, 68, 4210 10.1016/j.tet.2012.03.096
20. Ito, K.; Takahashi, M.; Hoshino, T.; Nishiki, M.; Ohba, Y. Lett. Org. Chem. 2006, 3, 735 10.2174/157017806779025898
21. Ichibakase, T.; Orito, Y.; Nakajima, M. Tetrahedron Lett. 2008, 49, 4427 10.1016/j.tetlet.2008.05.004
22. Li, W.; Rodriguez, S.; Duran, A.; Sun, X.; Tang, W.; Premasiri, A.; Wang, J.; Sidhu, K.; Patel, N. D.; Savoie, J.; Qu, B.; Lee, H.; Haddad, N.; Lorenz, J. C.; Nummy, L.; Hossain, A.; Yee, N.; Lu, B. Z.; Senanayake, C. H. Org. Process Res. Dev. 2013, 17, 1061 10.1021/op400055z
23. Schopohl, M. C.; Faust, A.; Mirk, D.; Fröhlich, R.; Kataeva, O.; Waldvogel, S. R. Eur. J. Org. Chem. 2005, 14, 2987 10.1002/ejoc.200500108
24. Kato, K.; Yamada, T.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 179 10.1246/bcsj.63.179
25. Hamilton, D. E.; Drago, R. S.; Zombeck, A. J. Am. Chem. Soc. 1987, 109, 374 10.1021/ja00236a014
26. Uchida, C.; Kitahashi, H.; Yamagishi, T.; Iwaisaki, Y.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 2775-2785 10.1039/p19940002775
27. Foti, C. J.; Fields, J. D.; Kropp, P. J. Org. Lett. 1999, 1, 903 10.1021/ol990823x
28. Heydari, A.; Mehrdad, M.; Maleki, A.; Ahmadi, N. Synthesis 2004, 10, 1563 10.1055/s-2004-822406
29. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1960, 82, 681 10.1021/ja01488a045
30. Brown, H. C.; Kim, S. C.; Krishnamurthy, S. J. Org. Chem. 1980, 45, 1 10.1021/jo01289a001
31. Lin, S.; Yang, Z.-Q.; Kwok, B. H. B.; Koldobskiy, M.; Crews, C. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6347 10.1021/ja049821k