Preparation of chiral amides and amines

Details Preparation of chiral amides and amines Preparation of chiral amides and amines

C - Chemistry, Metallurgy

07

C

C07C 233/00 (2006.01) C07C 235/00 (2006.01) C07C 237/00 (2006.01) C07C 239/00 (2006.01)

Patent

CA 2648121

This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1- naphthalenamine or 1,2,3,4-tetrahydro-l-naphthalenamine substructure.

La présente invention concerne un procédé commode de conversion d'oximes en énamides. Le procédé de nécessite pas l'utilisation de réactifs métalliques. En conséquence, il produit les composés souhaités sans production concomitante d'un large volume de déchets métalliques. Les énamides sont des précurseurs utiles des amides et amines. L'invention concerne un procédé de conversion d'un énamide prochiral en amide chiral correspondant. Dans un procédé exemplaire, un centre amino chiral est introduit durant l'hydrogénation à l'aide d'un catalyseur d'hydrogénation chiral. Dans des modes de réalisations sélectionnés, l'invention concerne des procédés de préparation d'amides et d'amines comprenant la sous-structure 1,2,3,4-tétrahydro-N-alkyl-1- naphthalénamine ou 1,2,3,4-tétrahydro-l-naphthalénamine.

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