Transition-metal-catalyzed C-C bonds formation via transfer hydrogenation : from methodology development to (+)-SCH 351448 synthesis

Redox-triggered carbonyl addition via transfer hydrogenation, which enables direct primary alcohol C-H functionalization to form C-C bond, avoids usage of premetalated reagents or discrete alcohol to aldehyde redox reactions. Moreover, step-economy could be greatly improved by site-selective transformations of polyfunctional molecules due to bypassing the need to install and remove protecting groups. However, the redox site-selective transformations still pose a significant challenge in the area of synthetic organic chemistry. Efforts have been focused on the development of iridium catalyzed transfer hydrogenative coupling reactions of primary alcohols with different allyl donors through carbonyl addition in a site-selective manner as well as ruthenium catalyzed regioselective hydrohydroxyalkylation of primary alcohols with a basic feedstock-styrene. Additionally, studies towards the total synthesis of type I polyketide natural product (+)-SCH 351448 in the most concise route is presented.Chemistr