Categories: C-N Bond Formation > Amines >
Synthesis of primary amines
Related |
|
 |
Name Reactions
| Two Steps: | |
 |
Mitsunobu Reaction |
 |
Staudinger Reaction |
Recent Literature
An efficient, general procedure for highly chemoselective reductive mono-alkylation of ammonia with ketones is reported. Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ reduction with sodium borohydride, and a simple workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes, on the other hand, afforded the corresponding symmetrical secondary amines
selectively.
B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron, 2004,
60, 1463-1471.
The synthesis of free α-chiral amines by a one-pot multicomponent procedure
involves the formation of N-diphenylphosphinoylimines from
commercially available starting materials and the subsequent
enantioselective addition of diakylzinc reagents using an air-stable
precatalyst complex.
. Cote, A. B. Charette, J. Org. Chem.,
2005,
70, 10864-10867.
The electrophilic
amination of Grignard reagents with 4,4,5,5-tetramethyl-1,3-dioxolan-2-one O-phenylsulfonyloxime
followed by acidic hydrolysis of the resulting imines gave primary amines.
M. Kitamura, T. Suga, S. Chiba, K. Narasaka, Org. Lett.,
2004,
6, 4619-4621.
