Stereocontrolled Cyclizations of 2-Propylidene-1,3-bis(silane)s

Montana State University, Bozeman MT

Investigators

Abstract

This project focuses on the development and synthetic applications of stereoselective iminium bis-(silane) cyclization and vanadium promoted free radical methylenecyclopentane annulations. Recent discoveries in the principal investigator's laboratory indicate that chiral and achiral 2-propylidene-1,3-bis(silane) bearing imines undergo efficient cyclization with superb levels of substrate directed stereocontrol in the presence of TiCl4. This project will continue the investigation of 2-propylidene-1,3-bis(silane) by studying the stereoselective bond forming reactions between 2-propylidene-1,3-bis(silane) and carbon based electrophiles. Once developed, such a methodology will be employed to synthesize structurally intricate isotropanes and their derivatives. The development of free radical methylenecyclopentane annulations promoted by the novel and highly economical vanadium reagent (CF3CH2O)VOCl2 is another objective of the project. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Tom Livinghouse, of the Department of Chemistry at Montana State University. Professor Livinghouse's research efforts revolve around the discovery, development, and exploitation of novel reactions for the synthesis of challenging natural products. Professor Livinghouse's bis(silane) cyclization strategy allows the efficient construction of complex molecules. The project is of considerable significance to the chemical and pharmaceutical industry, as it could impact how organic molecules are prepared.