The underlying goal of synthetic chemistry is to generate high-value compounds through the development of methods.  As the importance for natural products, pharmaceuticals, diagnostics, agrochemicals and other compounds continues to grow, a surgent in proficiency and efficiency demands new ways to prepare molecules.  Domino or cascade reactions represent a long-standing class of transformations that aim to overcome or bypass issues with purification and protecting groups through the generation of complexity in a one-pot sequence of coupling events.  One of the most simple, yet effective ways to accomplish diversity generating reactions is through multicomponent couplings which, for the purpose of this talk, will infer to mean three components or more in a single reaction vessel.  The concept of domino or cascade couplings can also be extended to substrate equals product and subsequent product can equal substrate for further complexity generation such as in an intramolecular cyclization event.  These green chemistry reactions have been embraced in the mantra of Diversity-Oriented Synthesis (DOS), which aims to capture that each product equals substrate can generate unique structures from a single reaction event. In this presentation, we will examine how microwaves can influence reacted motifs from cascade coupling events for further derivitization of products that equal substrates and utilize the knowledge gained to explore anomeric alkoxide glycosylation.  Furthermore, we will employ multicomponent cascade reactions containing chiral D-sugars for diastereoselective control in the formation of natural product-like compounds of high value.

Microwave-assisted multicomponent cascade couplings with carbohydrates

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.