Aldol Reaction of the Heavier Carbon Homologues

This application targets to study and explore the aldol reaction of heavier homologues of carbon. The classical carbon based aldol reaction is one of the most important biosynthetic tools for the evolution of life on earth. The generality associated with this process are among the most extensively investigated of all synthetic methods. For the heavier homologues of carbon, however, such bond-forming reactions were unknown until a recent study in our laboratories demonstrated that this reaction type is indeed possible. This new synthetic method can be seen as an interesting and powerful alternative to standard coupling techniques. Beyond its obvious utility for the synthesis of non-natural compounds, this aldol reaction can be both an engine and a proving ground for new methodological advances.

In the course of this project, a new strategy for the synthesis of group 14 acyl compounds with tailored properties was developed. In the process, additional powerful non-toxic photoinitiators were obtained. Furthermore, we performed follow-up reactions and gained access to novel group 14 compounds with non-symmetric substitution patterns that were previously inaccessible. In addition, we were able to synthesize the first example of a geminal bisenolate, which represents a new innovative building block for further projects and investigations. This work also provided access to previously unknown acylsilanes and acylgermanes, which served as precursors for inter- and intramolecular aldol reactions.