A facile one-pot synthesis of acyclic β-enamino ketones, an important class of versatile synthetic intermediates

A one-pot sequential process consisting of nucleophilic substitution of the lithiated acetylides with Weinreb amides followed by a Michael reaction of the extruded N-methoxy- N-methylamine after quenching with saturated NH 4Cl, provided β-enamino ( N-methoxy- N-methyl) ketones in high yield. It has...

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Bibliographic Details
Published in:Tetrahedron letters 2007-04, Vol.48 (17), p.3069-3072
Main Authors: Choudhury, Anusuya, Breslav, Michael, Grimm, Jeffrey S., Xiao, Tong, Xu, Dawei, Sorgi, Kirk L.
Format: Article
Language:English
Subjects:
Weinreb amide
β-Enamino ketones
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Summary:A one-pot sequential process consisting of nucleophilic substitution of the lithiated acetylides with Weinreb amides followed by a Michael reaction of the extruded N-methoxy- N-methylamine after quenching with saturated NH 4Cl, provided β-enamino ( N-methoxy- N-methyl) ketones in high yield. It has been demonstrated that this method is applicable to a wide variety of such amides and acetylides. Prolonged stirring of the reaction mixture with saturated NH 4Cl generates β-enamino ketones with structural diversity. A one-pot sequential process consisting of nucleophilic substitution of the lithiated acetylides with Weinreb amides followed by a Michael reaction of the extruded N-methoxy- N-methylamine after quenching with saturated NH 4Cl, provided β-enamino ketones in high yield and in a single geometrical isomeric form. It has been demonstrated that this method is applicable to a wide variety of such amides and to different acetylides.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.02.115