New Strategies for Hydroxyl-Directed Organic Reactions

Abstract

Described herein are four different research projects spanning over two different research groups. The first two projects describe the development and application of scaffolding catalysts for the (1) site-selective silylation of ribonucleosides and (2) the distal and diastereoselective hydroformylation of homoallylic alcohols. These projects emphasize the effectiveness of scaffolding catalysts to bind a hydroxyl-containing substrate and control the site- or regioselectivity of a reaction using said substrate. The third project describes a hydroxyl-directed diboration of homoallylic and bis-homoallylic alcohols. The hydroxyl-containing 1,2-bis(boronates) are valuable intermediates for further synthetic manipulations. One such manipulation, a hydroxyl-directed Suzuki cross-coupling reaction, is the focus of the final project. This directed cross-coupling reaction forges carbon-carbon bonds in a stereoselective manner, highlighted in the total synthesis of the naturally occurring compound, debromohamigeran E.