Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines
Bruhaspathy Miriyala, Sukanta Bhattacharyya* and John S. Williamson
*Department of Chemistry, Argonaut Technologies, 1101 Chess Drive, Foster
City, CA 94404, USA, Email: sbhattacharyya
argotech.com
B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron, 2004, 60, 1463-1471.
DOI: 10.1016/j.tet.2003.12.024
Abstract
Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ reduction with sodium borohydride allows a highly chemoselective reductive mono-alkylation of ammonia. A simple workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes afforded the corresponding symmetrical secondary amines selectively.
see article for more examples
H. J. Kumpaty, S. Bhattacharyya, E. W. Rehr, A. M. Gonzalez, Synthesis, 2003, 2206-2210.
Key Words
reductive amination, primary amines, benzylic amines, ammonia, sodium borohydride
ID: J72-Y2004-240
