Reductive N–O cleavage of Weinreb amides by sodium in alumina and silica gels: synthetic and mechanistic studies

Reductive N–O cleavage of Weinreb amides by sodium in alumina and silica gels: synthetic and mechanistic studies

[Display omitted] The use of sodium in alumina and silica gels for the reductive cleavage of the N–O bond of N-methoxy-N-methylamides, commonly referred to as Weinreb amides, has been investigated. This method reduces a diverse set of Weinreb amides with different functional groups to give modest to...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 56; no. 45; pp. 6227 - 6230
Main Authors: Jackson, James E., O’Brien, Brittany N., Kedzior, Sonya K., Fryz, Gage R., Jalloh, Fatmata S., Banisafar, Arash, Caldwell, Michael A., Braun, Max B., Dunyak, Bryan M., Dye, James L.
Format: Journal Article
Language:English
Published: Elsevier Ltd 04-11-2015
Subjects:
Alumina gel
Reduction
Silica gel
Sodium
Weinreb amide
DYDRCANRNSAYJA-UHFFFAOYSA-N
UZWAQQSVGQEZRY-UHFFFAOYSA-N
SIOAPROKUUGJAQ-UHFFFAOYSA-N
Weinreb amide
NCCHARWOCKOHIH-UHFFFAOYSA-N
JNXLTSSPACJLEG-BQYQJAHWSA-N
Reduction
PRCOHDSOXCGBAX-UHFFFAOYSA-N
Sodium
RWGJVMFILBWTGJ-UHFFFAOYSA-N
MXGRCIBAPXPYMA-UHFFFAOYSA-N
Alumina gel
Silica gel
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Summary:[Display omitted] The use of sodium in alumina and silica gels for the reductive cleavage of the N–O bond of N-methoxy-N-methylamides, commonly referred to as Weinreb amides, has been investigated. This method reduces a diverse set of Weinreb amides with different functional groups to give modest to excellent yields. In the course of the studies to explore mechanisms and functional group tolerance, an apparently novel group transfer emerged, implying base-promoted cleavage of the Weinreb amide to form formaldehyde, followed by aldol condensation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.099