Transforming cyclopropanes to enamides via σ-C-C bond eliminative borylation.
basic_science · Level V
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- Record sourced from PubMed, PMID 39191737.
- Also identified by DOI 10.1038/s41467-024-51484-6 and PMC identifier 11350172.
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Abstract
Recent strides in C-H borylation have significantly expanded our toolkit for the preparation of organoboronates. Nevertheless, avenues alternative to obtain these compounds via σ-C-C cleavage, thereby facilitating molecular scaffold editing, remain scarce. Several methodologies have been proposed for hydroboration of cyclopropanes by activating C-C bonds, conventionally relying on noble and hazardous metal catalysts to control reaction outcomes. Here, we present a strategy for crafting stereochemically precise γ-borylenamides through ring-opening of cyclopropanes avoiding any metallic entities. Boryl species, generated through a ternary reaction with BCl<sub>3</sub>, cyclopropanes, and a tertiary amine, selectively undergo C-C bond eliminative borylation under the directing of N-acyl group, thereby ensuring enhanced selectivity and efficiency along the reaction pathway. Such inherently stereoconvergent approach accommodates precursors of diverse geometries, including cis/trans isomeric blends.