[PDF] Semi-catalytic reduction of secondary amides to imines and aldehydes

What is reduction of N-methoxy-N-methyl amides?

Reduction of N-methoxy-N-methyl amides, also known as Weinreb amides, is one of the most frequent means of converting a carboxylic acid to an aldehyde. Nitriles are reduced to imines, which hydrolyze upon work-up to furnish aldehydes. Cl 1. DIBAL, ether CH2Cl2, –78 °CTBSO O Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem.,

Which amides are treated with DIBALH?

Accordingly, aromatic N,N-dimethylamide, morpholine amide, and Weinreb amides containingester moiety were treated with DIBALH and successive chemo-selective reduction was a?orded from amide groups leavingesters unreactive in most cases (entries 1–3 in Table 5).

How tertiary amides are reduced to corresponding aldehydes with lteah?

Tertiary amides are ef?ciently reduced to the corresponding aldehydes with LTEAH. LTEAH is formed by the reaction of 1 mole of LAH solution in ethyl ether with 3 moles of ethyl alcohol or 1.5 moles of ethyl acetate.

Can Schwartz reagents selectively reduce amidesto aldehydes?

Recently, the Schwartz(Cp2Zr(H)Cl) reagent6 andin situ-prepared Schwartz reagents7showed promising results in the selective reduction of amidesto aldehydes.