Protecting-group-free synthesis of amines: synthesis of primary amines from aldehydes via reductive amination.
New methodology for the protecting-group-free synthesis of primary amines is presented. By optimizing the metal hydride/ammonia mediated reductive amination of aldehydes and hemiacetals, primary amines were selectively prepared with no or minimal formation of the usual secondary and tertiary amine byproduct. The methodology was performed on a range of functionalized aldehyde substrates, including in situ formed aldehydes from a Vasella reaction. These reductive amination conditions provide a valuable synthetic tool for the selective production of primary amines in fewer steps, in good yields, and without the use of protecting groups.
Dangerfield
Emma M
EM
Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
Plunkett
Catherine H
CH
Win-Mason
Anna L
AL
Stocker
Bridget L
BL
Timmer
Mattie S M
MS
D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines