Year: 2026
Type: preprint
Abstract: Chiral alkanes bearing two contiguous tertiary all-carbon stereocentres are important motifs in bioactive molecules, natural products and functional compounds, yet their stereocontrolled synthesis remains challenging. Here we report their modular preparation through the formal deoxygenative dialkylation of enantioenriched vinyl epoxides. Two consecutive organocopper-mediated S N 2′ substitutions enable stereospecific transfer of the starting stereochemical information followed by diastereoselective installation of the adjacent stereocentre. The sequence can be performed in one pot, providing densely substituted hydrocarbon frameworks with high regio- and stereocontrol. The method accommodates diverse, including sterically demanding, alkyl substituents, extends to cyclic substrates, and leaves a terminal alkene for downstream diversification. Vinyl epoxides thus provide a stereochemically encoded platform for straightforward access to complex chiral alkanes.
Source: ChemRxiv
Authors: Nicolò Rossi, Gwilherm Evano
Institution: Université Libre de Bruxelles
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G6535406996, G8248950111, G956224935
OpenAlex ID: W7220417303