ArticleAngewandte Chemie (International ed. in English)2022
Catalytic Asymmetric β-Oxygen Elimination.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Zipper polydefluorination-monoborylation of perfluoroalkyl chains.Nature communications · 2026Article
- Catalytic Asymmetric Ring-Opening Reactions of Unstrained Heterocycles Using Cobalt Vinylidenes.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic Asymmetric β-Oxygen Elimination.Angewandte Chemie (International ed. in English) · 2022Article
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Abstract
A catalytic enantioselective β-O-elimination reaction is reported in the form of a zirconium-catalyzed asymmetric opening of meso-ketene acetals. Furthermore, a regiodivergent β-O-elimination is demonstrated. The reaction proceeds under mild conditions, at low catalyst loadings, and produces chiral monoprotected cis-1,2-diols in good yield and enantiomeric excess. The combination with a Mitsunobu reaction or a one-pot hydroboration/Suzuki reaction sequence then gives access to additional diol and aminoalcohol building blocks. A stereochemical analysis supported by DFT calculations reveals that a high selectivity in the hydrozirconation step is also important for achieving high enantioselectivity, although it does not constitute the asymmetric step. This insight is crucial for the future development of related asymmetric β-elimination reactions.
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