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2004
Amines
Q 0120
47- 070
A Selective Reductive Amination of Aldehydes by the Use of Hantzsch Dihydropyridines as Reductant. — The direct reductive amination of aldehydes and ketones
using the Hantzsch dihydropyridine as reductant and a catalytic amount of scandium
triflate is reported. The reaction proceeds smoothly in THF and CH2Cl 2 without reduction of any other functional groups like nitro or cyano groups. In addition, acidic functional groups (phenolic OH and carboxyl group) do not affect the product yield. Further,
the reaction is highly selective towards aldehydes over ketones, cf. preparation of (VII).
The present reaction is also proved to be useful for the reductive amination of polyamino compounds such as (VIII). — (ITOH, T.; NAGATA, K.; MIYAZAKI, M.;
ISHIKAWA, H.; KURIHARA, A.; OHSAWA*, A.; Tetrahedron 60 (2004) 31,
6649-6655; Sch. Pharm. Sci., Showa Univ., Shinagawa, Tokyo 142, Japan; Eng.) —
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