A new method of partial and chemoselective reduction of nitriles to aldehydes by lithium diisobutyl-iso-propoxyaluminum hydride (LDBIPA)

Bulletin of the Korean Chemical Society

Volumn 31, Issue 2, 2010, Pages 473-474

  Choi, Young Mi ^a   Yoo, Min ^a   An, Duk Keun ^a  

^a Kangwon National University   (South Korea)

Author keywords

Aldehyde; Chemoselectivity; Lithium diisobutyl iso propoxyaluminum hydride; Nitrile; Partial reduction

Indexed keywords

EID: 77951778918     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.02.473     Document Type: Article

References (29)

1. Kim, M. S.; Choi, Y. M.; An, D. K. Tetrahedron Lett. 2007, 48, 5061;
2. Song, J. I.; An, D. K. Chem. Lett. 2007, 36, 886;
3. Chae, M. J.; Song, J. I.; An, D. K. Bull. Korean Chem. Soc. 2007, 28, 2517;
4. Choi, S. J.; Lee, S. D.; An, D. K. Bull. Korean Chem. Soc. 2008, 29, 1449.
5. Choi, Y. M.; Kim, M. E.; An, D. K. Bull. Korean Chem. Soc. 2009, 30, 2825.
6. Sodium ethoxyaluminumhydride: Hesse, G.; Schrodel, R. Angew. Chem. 1956, 68, 438.
7. Lithium triethoxyaluminum hydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 68, 438;
8. Brown, H. C. J. Chem. Educ. 1961, 38, 173;
9. Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1085;
10. de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
11. Sodium diethylaluminohydride in the presence of 2,6- di-t- butylphenoxydiethylaluminium: Yoon, N. M.; Kim, S. K.; Kyong, Y. S. Bull. Korean Chem. Soc. 1986, 7, 323.
12. Organosilicon hydride: Fry, J. L. Chem. Comm. 1974, 45;
13. Fry, J. L.; Ott, R. A. J. Org. Chem. 1981, 46, 602.
14. Thexylbromoborane-dimethyl sulfide: Cha, J. S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301.
15. Potassium 9-sec-amyl-9-boratabicyclo- [3.3.1]nonane: Cha, J. S.; Yoon, M. S. Tetrahedron Lett. 1989, 30, 3677.
16. Lithium tris(dihexylamino)aluminum hydride: Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670.
17. Sodium diethylpiperidinohydroaluminate: Yoon, N. M.; An, D. K.; Jeong, K. H. Bull. Korean Chem. Soc. 1994, 14, 302.
18. Diisobutylaluminum hydride: Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR, 1957, 116, 422;
19. Minato, H.; Nagasaki, T. J. Chem. Soc. [c] 1966, 1866;
20. Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pats-Bas 1966, 85, 343;
21. Miller, A. E. G.; Bliss, J. W.; Achwartzman, L. H. J. Org. Chem. 1959, 24, 627;
22. Tesseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44;
23. Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org Chem. 1970, 35, 186;
24. Stevens, R. V.; Dupree Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977;
25. Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
26. Diisobutylaluminum hydride-dimethyl sulfide complex: Cha, J. S.; Kwon, O. O.; Jeoung, M. K.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 1021.
27. N,N'-Dimethylethylenediaminoaluminum hydride: Cha, J. S.; Jang, S. H.; Kwon, S. Y. Bull. Korean Chem. Soc. 2002, 23, 1697.
28. Catecholalane: Cha, J. S.; Chang, S. W.; Kwon, O. O.; Kim, J. M. Synlett 1996, 165.
29. Lithium diisobutylpiperidinohydroaluminate: Ha, J. H.; Ahn, J. H.; An, D. K. Bull. Korean Chem. Soc. 2006, 27, 121.