Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides

In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and more practical than standard silylformylation reactions. It overall represents a versatile and rapid access to various tetrasubstituted 3-silyl-2-amidoacrolein derivatives. The synthetic potential of these new building blocks has been evaluated by performing several postfunctionalization.

Automated summary

This study presents a novel regio- and stereoselective silylformylation reaction of ynamides, demonstrating good tolerance to functional groups. Substitution of CO by an isocyanide enhances the safety and practicality of this reaction, providing a rapid access to various tetrasubstituted 3-silyl-2-amidoacrolein derivatives. The synthetic potential of these new building blocks has been evaluated through postfunctionalization.