Lithium borohydride: a reagent of choice for the selective reductive amination of cyclohexanones

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7134-7136

  Cabral, Shawn ^a   Hulin, Bernard ^a   Kawai, Makoto ^a  

^a Department of Cardiovascular and Metabolic Diseases ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; LITHIUM DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; REDUCTION KINETICS; SUBSTITUTION REACTION;

EID: 34548389276     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.217     Document Type: Article

References (8)

1. Wu Y.-D., and Houk K. J. Am. Chem. Soc. 109 (1987) 908 and references therein
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3. Wigfield D.C. Tetrahedron 35 (1979) 449
4. Wrobel J.E., and Ganem B. Tetrahedron Lett. 22 (1981) 3447-3450
5. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
6. 3) 7.37-7.22 (m, 5H), 3.83 (s, 2H), 2.45 (m, 1H), 2.05 (d, 2H), 1.75 (d, 2H), 1.15 (m, 2H), 1.00 (m, 3H), 0.82 (s, 9H).
7. The reducing agent in these reactions is probably borohydride itself rather than mono-, di-, or trimethoxyborohydride, since borohydride reacts slowly with methanol at low temperatures:. Schlesinger H.I., Brown H.C., Hoekstra H.R., and Rapp L. J. Am. Chem. Soc. 75 (1953) 199-204 Switching the solvent to ethanol had no effect on the isomer ratio
8. In most cases the ratio of trans-isomer was improved further upon formation of the hydrochloride salt.