Categories: C-N Bond Formation > Amines >
Synthesis of primary amines
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Name Reactions
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Mitsunobu Reaction |
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Staudinger Reaction |
Recent Literature
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.
B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron, 2004,
60, 1463-1471.
An experimentally simple Microwave-assisted reductive alkylation of methyl
carbamate with a range of aldehydes provides, after basic work-up, structurally
diverse primary amines. This method is particularly amenable to high-throughput
synthesis.
F. Lehmann, M. Scobie, Synthesis, 2008,
1679-1681.
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.
An 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 gives primary amines.
M. Kitamura, T. Suga, S. Chiba, K. Narasaka, Org. Lett.,
2004,
6, 4619-4621.
