Issue 29, 2022

Metal-free stereoselective addition of propiolic acids to ynamides: a concise synthetic route to highly substituted enediyne/dienyne-(E)-N,O-acetals

Abstract

A straightforward and sustainable approach for the 1,2-addition of propiolic acids to ynamide has led to bench-stable sp2 (E)-enol-enamides of enediynes and dienynes. The reaction is chemo-, regio-, and stereoselective and does not require metal catalysts and solvent. The ynamide motif is extremely amenable to functionalization in the presence of the tethered alkyne triple bond. The synthetic technique is operationally simple; no hydrolysis of ketenimine species occurs under acidic conditions. The transformation tolerates a wide range of common functional groups, constructing a library of highly functionalized 1,5,5′/6′-enediynes and 1,5,5′-dienynes of sp2 (E)-N,O-acetal skeletons.

Graphical abstract: Metal-free stereoselective addition of propiolic acids to ynamides: a concise synthetic route to highly substituted enediyne/dienyne-(E)-N,O-acetals

Supplementary files

Article information

Article type
Paper
Submitted
29 apr 2022
Accepted
17 jún 2022
First published
23 jún 2022

New J. Chem., 2022,46, 13981-13986

Metal-free stereoselective addition of propiolic acids to ynamides: a concise synthetic route to highly substituted enediyne/dienyne-(E)-N,O-acetals

R. Prasad, S. Kanikarapu, S. Dutta, S. Vangara and A. K. Sahoo, New J. Chem., 2022, 46, 13981 DOI: 10.1039/D2NJ01907H

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