Deoxygenative Dialkylation of Vinylic Epoxides to Chiral Alkanes by Double SN2’
- 1Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB, Avenue F. D. Roosevelt 50, Brussels, Belgium, 1050
- 2WEL Research Institute, Avenue Pasteur 6, Wavre, Belgium, 1300
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.
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BibTeX
@misc{rossi2026deoxygenative,
title = {{Deoxygenative Dialkylation of Vinylic Epoxides to Chiral Alkanes by Double SN2’}},
author = {Nicolò Rossi and Gwilherm Evano},
howpublished = {ChemRxiv},
year = {2026},
month = oct,
doi = {10.26434/chemrxiv.15009886/v1},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009886/v1},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Deoxygenative Dialkylation of Vinylic Epoxides to Chiral Alkanes by Double SN2’
AU - Nicolò Rossi
AU - Gwilherm Evano
PY - 2026
DA - 2026/10/05
PB - ChemRxiv
DO - 10.26434/chemrxiv.15009886/v1
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009886/v1
AB - 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.
ER -