ArticleAngewandte Chemie (International ed. in English)2020
Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements.
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 7 papers.
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7 citing papers in PubMed.
- Rhodium-Catalyzed Allylic Amination for the Enantioselective Synthesis of Tertiary β-Fluoroamines.Organic letters · 2025Article
- Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines.Nature communications · 2024Article
- Recent Advances in the Synthesis of Di- and Trisubstituted Hydroxylamines.Molecules (Basel, Switzerland) · 2023Review
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- Stereoretentive Regio- and Enantioselective Allylation of Isoxazolinones by a Planar Chiral Palladacycle Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements.Angewandte Chemie (International ed. in English) · 2020Article
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3 authors.
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Abstract
Chiral acyclic tertiary allylic alcohols are very important synthetic building blocks, but their enantioselective synthesis is often challenging. A major limitation in catalytic asymmetric 1,2-addition approaches to ketones is the enantioface differentiation by steric distinction of both ketone residues. Herein we report the development of a catalytic asymmetric Meisenheimer rearrangement to overcome this problem, as it proceeds in a stereospecific manner. This allows for high enantioselectivity also for the formation of products in which the residues at the generated tetrasubstituted stereocenter display a similar steric demand. Low catalyst loadings were found to be sufficient and the reaction conditions were mild enough to tolerate even highly reactive functional groups, such as an enolizable aldehyde, a primary tosylate, or an epoxide. Our investigations suggest an intramolecular rearrangement pathway.
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