We are interested in making an acrylamide from an aldehyde and a diethyl phosphonate bearing a carboxamide in the beta-position. Our typical Horner Wadsworth Emmons conditions are similar to what Masamune, Roush, and their collaborators did (Blanchette et al., Tetrahedron 1984 25(21) 2183-86), and similar conditions have since been used by many groups. The typical conditions are LiX and a tertiary amine base. Esters are tolerated, but I was wondering about the acidity of the hydrogen on the nitrogen atom and whether this might be a problem. In the 1984 paper there was one aldehyde which had a secondary amide elsewhere in the molecule. And the 1995 paper (see next paragraph) is also suggestive of success. So maybe a carboxamide is fine.
Although my literature searching was not as extensive as it might have been, I did turn up one paper that used similar chemistry in the solid phase. The solid support was attached to the nitrogen atom of the phosphonate. They used a 10-fold excess of aldehyde, and they used P-31 NMR to detect (Johnson CR, Zhang, B, 1995 Tet Lett 36(51) 9253-9256). We would not work in the solid phase. Most conditions that we have used for solution HWE reactions have used a slight excess of phosphonate over the aldehyde, although the opposite was true for one reaction.