Lithium amidotrihydroborate, a powerful new reductant. Transformation of tertiary amides to primary alcohols

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3623-3626

  Myers, Andrew G ^a   Yang, Bryant H ^a   Kopecky, David J ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; AMINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0029989131     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00652-1     Document Type: Article

References (19)

1. (a) Uffer, H.; Schlittler, E. Helv. Chim. Acta 1948, 31, 1397.
2. (b) Gaylord, N. G. Reductions with Complex Metal Hydrides Wiley-Interscience: New York, 1956, p. 544-592.
3. (c) Zabicky, J., Ed. The Chemistry of Amides Wiley-Interscience: New York, 1970, p. 795-801.
4. (a) Brown, H. C.; Heim, P. J. Am. Chem. Soc. 1964, 86, 3566.
5. (b) Brown, H. C.; Narasimhan, S.; Choi, Y. M. Synthesis 1981, 441.
6. (c) Brown, H. C.; Narasimhan, S.; Choi, Y. M. Synthesis 1981, 996.
7. Brown, H. C.; Kim, S. C. Synthesis 1977, 635.
8. (a) Hutchins, R. O.; Learn, K.; El-Telbany, F.; Stercho, Y. P. J. Org. Chem. 1984, 49, 2438.
9. (b) Fisher, G. B.; Harrison, J.; Fuller, J. C.; Goralski, C. T.; Singaram, B. Tetrahedron Lett. 1992, 33, 4533.
10. (c) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Goralski, C. T.; Singaram, B. Tetrahedron Lett. 1993, 34, 1091.
11. (d) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhardt, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378.
12. Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
13. 1H NMR spectroscopy.
14. (a) Pross, A.; Radom, L. Tetrahedron 1980, 36, 673.
15. (b) Armstrong, D. R.; Perkins, P. G.; Walker, G. T. J. Mol. Struct. 1985, 122, 189.
16. Srebnik, M.; Cole, T. E.; Veeraraghavan, R.; Brown, H. C. J. Org. Chem. 1989, 54, 6085.
17. (a) Andrews, G. C.; Crawford, T. C. Tetrahedron Lett. 1980, 21, 693.
18. (b) Andrews, G. C. Tetrahedron Lett. 1980, 21, 697.
19. Stetter, H.; Schwarz, M.; Hirschorn, A. Chem. Ber. 1959, 92, 1629.