ArticleOrganic letters2019
Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.
Article in Organic letters, 2019. 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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Who cites it
7 citing papers in PubMed.
- Copper-Catalyzed Diastereo-, Enantio-, and (Journal of the American Chemical Society · 2024Article
- Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.ACS catalysis · 2022Article
- Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- A Diastereodivergent and Enantioselective Approach toJournal of the American Chemical Society · 2021Article
- Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.Organic letters · 2021Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.Chemical science · 2020Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By employing N-heterocyclic carbenes as ligands for the Cu catalyst, good branched selectivity can be obtained with high diastereocontrol. This methodology allows access to a catalytically generated, polarity-reversed (umpolung) allyl nucleophile to enable the preparation of chiral 1,2-aminoalcohol synthons containing a dissonant functional group relationship.
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Registered trials
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