Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C–H oxidation

The ubiquitous nature of C-H bonds in organic molecules makes them attractive as a target for rapid complexity generation, but brings with it the problem of achieving selective reactions. In developing new methodology for C-H functionalization, alkenes are an attractive starting material due to their abundance and low cost. Here we describe the conversion of 1-alkenes into 1,4-diols. The method involves the installation of a Si,N-type chelating auxiliary group on the alkene followed by iridium catalyzed C-H silylation of an unactivated δ-C(sp(3))-H bond to produce an silolane intermediate. Oxidation of the C-Si bonds affords a 1,4-diol. The method is demonstrated to have broad scope and a good functional group compatibility by application to the selective 1,4-oxygenation of several natural products and derivatives.