"For this work, we developed a three-component coupling reaction of 1,3-dienes (isoprene and its derivatives), a diboron reagent, and ketones: and converted these substrates to value-added chiral tertiary homoallylic alcohols," said corresponding author Martin Oestreich. "These serve as common building blocks for the synthesis of a variety of natural products and pharmaceutically relevant compounds."
In particular, this holds the potential to help overcome a drug discovery bottleneck related to screening small molecules, due to their ability to bind to a preselected protein target. This increases the efficiency and reduces the overall cost of preparing new small molecules with a particular configuration.
Oestreich said: "If a molecule contains two asymmetric centres, there are up to four possible stereoisomers. Different stereoisomers – while very closely related chemically – can have vastly different properties. For example, one could be a medicinally useful drug while the other could cause harm in the human body.
"Lack of efficient access to collections of synthetic compounds that display stereochemical diversity is a key bottleneck in the small-molecule [drug] discovery process. In this work, we realize the controlled formation of the two possible diastereomers, each in highly enantioenriched form, from a common set of precursors by employing different ligands."
This article is free to read in our open access, flagship journal Chemical Science: Jian‐Jun Feng, Yan Xu et al., Chem. Sci., 2019, Advance Article. DOI: 10.1039/ C9SC03531A. You can access our 2019 ChemSci Picks in this article collection.