Rhodium-catalyzed hydrocarbonylation of a homoallylamine via n-h activation and application for synthesis of yohimbane alkaloids

Organometallics

Volumn 33, Issue 16, 2014, Pages 4240-4244

  Chiou, Wen Hua ^a   Wang, Yu Wei ^a   Kao, Chien Lun ^a   Chen, Po Chou ^a   Wu, Chen Chang ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDRIDES;

HOMOALLYL AMINE; METAL HYDRIDES; N-H ACTIVATION; OXIDATIVE CLEAVAGES; RHODIUM-CATALYZED;

RHODIUM;

EID: 84906545252     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500498u     Document Type: Article

References (38)

1. Ojima, I. In Catalytic Asmmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
2. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2004.
3. In Handbook of Cyclization Reactions; Ma, S., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2010.
4. Eilbracht, P.; Barfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329-3365
5. Ojima, I.; Tsai, C.-Y.; Tzamarioudaki, M.; Bonafoux, D. In Organic Reactions, 1 st ed.; Overman, L. E., Ed.; John Wiley & Sons: New York, 2000; 56, pp 1-354.
6. Breit, B.; Seiche, W. Synthesis 2001, 1-36
7. Chiou, W.-H.; Lee, S.-Y.; Ojima, I. Can. J. Chem. 2005, 83, 681-692
8. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186
9. Knifton, J. F. J. Organomet. Chem. 1980, 188, 223-236
10. Krafft, M. E.; Wilson, L. J.; Onan, K. D. Tetrahedron Lett. 1988, 29, 6421-6424
11. Zhou, J. Q.; Alper, H. J. Org. Chem. 1992, 57, 3328-3331
12. Zhang, Z.; Ojima, I. J. Organomet. Chem. 1993, 454, 281-289
13. Baxter, E. W.; Marino, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag: New York, 1992; 8, p 197.
14. Baxter, E. W.; Labaree, D.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 7682-7692
15. Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1999, 64, 3237-3243
16. Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998-7007
17. Chen, H.-W.; Hsu, R.-T.; Chang, M.-Y.; Chang, N.-C. Org. Lett. 2006, 8, 3033-3035
18. Miyafuji, A.; Ito, K.; Katsuki, T. Heterocycles 2000, 52, 261-272
19. Tanaka, M.; Toyofuku, E.; Demizu, Y.; Yoshida, O.; Nakazawa, K.; Sakai, K.; Suemune, H. Tetrahedron 2004, 60, 2271-2281
20. Martin, S. F.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170-5180
21. Meyers, A. I.; Highsmith, T. K.; Buonora, P. T. J. Org. Chem. 1991, 56, 2960-2964
22. Sparks, S. M.; Shea, K. J. Tetrahedron Lett. 2000, 41, 6721-6724
23. Padwa, A.; Beall, L. S.; Heidelbaugh, T. M.; Liu, B.; Sheehan, S. M. J. Org. Chem. 2000, 65, 2684-2695
24. Lounasmaa, M.; Jokela, R. Tetrahedron 1990, 46, 615-622
25. Stork, G.; Livingston, D. A. Chem. Lett. 1987, 105-108
26. Aube, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009-9018
27. Yamaguchi, R.; Hamasaki, T.; Sasaki, T.; Ohta, T.; Utimoto, K.; Kozima, S.; Takaya, H. J. Org. Chem. 1993, 58, 1136-1143
28. Naito, T.; Miyata, O.; Tada, Y.; Nishiguchi, Y.; Kiguchi, T.; Ninomiya, I. Chem. Pharm. Bull. 1986, 34, 4144-4149
29. Kaoudi, T.; Miranda, L. D.; Zard, S. Z. Org. Lett. 2001, 3, 3125-3127
30. Isobe, M.; Fukami, N.; Goto, T. Chem. Lett. 1985, 1, 71-74
31. Kametani, T.; Suzuki, T.; Unno, K. Tetrahedron 1981, 37, 3819-3923
32. Medarde, M.; Caballero, E.; Tomé, F.; García, A.; Montero, M. J.; Carrón, R.; Feliciano, A. S. Eur. J. Med. Chem. 1993, 28, 887-892
33. Leeuwen, P. W. N. M. v.; Claver, C. In Rh-Catalyzed Hydroformylation; Leeuwen, P. W. N. M. v.; Claver, C., Eds.; Kluwer Academic Publishers: Dordrecht, 2002.
34. Sanches-Delgado et al. proposed a mechansitic study for the cyclization of N -alkylallylamines under syn gas. See: Sánchez-Delgado, R. A.; Rosa, R. G. d.; Ocando-Mavarez, E. J. Mol. Catal. 1996, 108, 125-129
35. For the preparation of deuterium-labeled dione, see: Baldwin, J. E.; Kaplan, M. S. J. Am. Chem. Soc. 1971, 93, 3969-3977
36. Krafft, M. E.; Wilson, L. J.; Onan, K. D. Organometallics 1988, 7, 2528-2534
37. A Rh(V) species should be involved in the H-D exchange process. For a Rh(V) species, see: Duckett, S. B.; Haddleton, D. M.; Jackson, S. A.; Perutz, R. N.; Poliakoff, M.; Upmacis, R. K. Organometallics 1988, 7, 1526-1532
38. Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655