The First Practical Niobium(III) Reagent in Organic Synthesis: A Convenient Route to 2-Amino Alcohols via the Coupling of Imines with Aldehydes or Ketones Promoted by NbC13(DME)

Journal of the American Chemical Society

Volumn 109, Issue 21, 1987, Pages 6551-6553

  Roskamp, Eric J ^a   Pedersen, Steven F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281646     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00255a073     Document Type: Article

References (11)

1. For reviews, see; (a) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. (b) Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods; Scheffold, R., Ed.; Wiley; New York, 1983; Vol. 3. (c) Lai, Y. H. Org. Prep. Proc. Int. 1980. 112. 361. (d) Ho. T. L. Synthesis 1979. 1.
2. Nugent, W. A.; Thorne, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788 and references therein, (b) Famili, A.; Farona, M. F.; Thanedar, S. J. Chem. Soc., Chem. Commun. 1983, 435.
3. See ref 2a. (b) Negishi, E.; Swanson, D. R.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1987, 28, 917. (c) Negishi, E.; Cederbaum, F. E.; Takahashi, T. J. Am. Chem. Soc. 1986, 27, 2829. (d) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A. J. Am. Chem. Soc. 1985, 107, 2568.
4. Allen, A. D.; Naito, S. Can. J. Chem., 1976, 54, 2948. (b) Maas, E. T., Jr.; McCarley R. E. Inorg. Chem. 1973, 12, 1096.
5. For examples, see: (a) Cotton, F. A.; Diebold, M. P.; Matusz, M.; Roth, W. J. Inorg. Chim. Acta 1986, 112, 147. (b) Cotton, F. A.; Diebold, M. P.; Llusar, R.; Roth, W. J. J. Chem. Soc., Chem. Commun. 1986, 1276. (c) Cotton, F. A.; Diebold, M. P.; Roth, W. J. Inorg. Chem. 1985, 24, 3509. (d) Cotton, F. A.; Duraj, S. A.; Roth, W. J. J. Am. Chem. Soc. 1984, 106, 6987. (e) Cotton, F. A.; Duraj, S. A.; Roth, W. J. Can. J. Chem., 1984, 106, 4749. (f) Cotton, F. A.; Duraj, S. A.; Roth, W. J. Can. J. Chem., 1984, 106, 3527. (g) Cotton, F. A.; Roth, W. J. Inorg. Chim. Acta 1984, 85, 17. (h) Cotton, F. A.; Hall, W. T.; Cann. K. J.; Karol. F. J. Macromolecules 1981. 14. 233.
6. For other examples where Bu3SnH has been used to reduce an inorganic halide, see: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152 (Supplementary Material), (b) Roth, A.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Am. Chem. Soc. 1986, 108, 6823. (c) Fjeldberg, T.; Haaland, A.; Schilling, B. E. R.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Dalton Trans. 1986, 1551.
7. Durfee, L. D.; Fanwick, P. E.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 4720. (b) Mayer, J. M.; Curtis, C. J.; Bercaw, J. E. J. Am. Chem. Soc. 1983, 105, 2651. (c) Chiu, K. W.; Jones, R. A.; Wilkinson, G.; Galas, A. M. R.; Hursthouse, M. B. J. Chem. Soc. Dalton 1981, 2088. (d) Takahashi, Y.; Onoyama, N.; Ishikawa, Y. Chem. Lett. 1978, 525. (e) Wolczanski, P. T.; Bercaw, J. E. J. Am. Chem. Soc. 1979, 101, 6450.
8. The Bu3SnH was prepared from Bu3SnCl/LiAlH4(Kuivila, H. G. Synthesis 1970, 499) or (Bu3Se)2O/polymethylhydrosiloxane (Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81) or purchased from Aldrich Chemical Company.
9. N-Debenzylation: (a) Ram, S.; Spicer, L. D. Tetrahedron Lett. 1987, 28, 515. (b) Adger, B. M.; O'Farrell, C.; Lewis, N. J.; Mitchell, M. B. Synthesis 1987, 53. (c) Mukaiyama, T.; Goto, Y.; Shoda, S. Chem. Lett. 1983, 671. N-Deallylation: Laguzza, B. C.; Ganem, B. Tetrahedron Lett. 1981, 22, 1483.
10. lower-valent metals, see: (a) Brunner, H.; Wachter, J.; Schmidbauer, J. Organometallics 1986, 5, 2212 and references therein. (b) Sielisch, T.; Behrens, U. J. Organomet. Chem. 1986, 310, 179.
11. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.