Cycloadditions Of Epoxy And Aziridinyl Enolsilanes

Abstract

<p>Cyclic structures are fundamental frameworks of many natural products, bioactive molecules and<br>drugs. Methodologies to assemble these architectures bearing functional groups that facilitate<br>additional transformations are needed, and synthetic routes towards such target compounds are often<br>built around the key reactions that provide access to the rings.[1,2]<br>Our group has been working on the cycloadditions, particularly intramolecular cycloadditions, that<br>employ epoxy or aziridinyl enolsilanes as dienophiles. Governed by the stereochemistry of the oxirane<br>or aziridine, these reactions ultimately contribute stereo-defined 1,3-hydroxy or 1,3-aminocarbonyl<br>motifs to provide seven-membered cycloadducts.[3] We have applied this reaction towards the<br>synthesis of some natural products.[4]<br>We have also found that epoxy or aziridinyl enolsilanes react as enophiles in (3+2) cycloadditions with<br>acyclic dienes and olefins.[5] In this presentation, we will report the latest developments of the<br>reactions of these epoxy and aziridinyl enolsilanes, as well as our efforts towards applying these<br>cycloadditions to the synthesis of natural products.<br></p>