ArticleAngewandte Chemie (International ed. in English)2020
Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- A promising dual catalytic "Isothiourea + X" platform: from classic ionic to radical transformations.RSC advances · 2026Review
- Enantioselective Synthesis in Continuous Flow: Polymer-Supported Isothiourea-Catalyzed Enantioselective Michael Addition-Cyclization with α-Azol-2-ylacetophenones.Organic process research & development · 2024Article
- Kinetics and Mechanism of Azole n-π*-Catalyzed Amine Acylation.Journal of the American Chemical Society · 2023Article
- Enantioselective rhodium-catalyzed addition of arylboronic acids toChemical science · 2023Article
- Kinetic resolution of racemic tertiary allylic alcohols through SChemical science · 2022Article
- Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.Nature communications · 2021Article
- Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane.Beilstein journal of organic chemistry · 2021Article
- Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.Angewandte Chemie (International ed. in English) · 2020Article
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6 authors.
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Abstract
A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.
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