The goal of this study is to establish a general protocol whereby N-substituted or (ultimately) N-unsubstituted amide functions may be directly emplaced at molecular carbonyl sites (to form alpha-hydroxyamides) or at imino sites (to form alpha-aminoamides). Amide-containing compounds (or the corresponding amines obtainable by amide reduction) are widely distributed amongst valuable therapeutic agents. The application of carbamoylsilanes to this end will be explored by extending successful preliminary results to a wide spectrum of candidate co-reactants under catalytic or noncatalytic conditions with a view towards maximizing output yields under the mildest possible conditions. Exploratory experiments directed towards inducing chiral stereoselectivity within these transformations will also be carried out.
| Cunico, Robert F; Pandey, Rajesh K (2005) Palladium-catalyzed synthesis of alpha-iminoamides from imidoyl chlorides and a carbamoylsilane. J Org Chem 70:5344-6 |
| Cunico, Robert F; Pandey, Rajesh K (2005) Palladium-catalyzed conversion of benzylic and allylic halides into alpha-aryl and beta,gamma-unsaturated tertiary amides by the use of a carbamoylsilane. J Org Chem 70:9048-50 |
| Chen, Jianxin; Cunico, Robert F (2004) Synthesis of alpha-ketoamides from a carbamoylsilane and acid chlorides. J Org Chem 69:5509-11 |
