ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 14 citations in OpenAlex.
- Kinetic Resolution of β-Branched Aldehydes through Peptide-Catalyzed Conjugate Addition Reactions.Journal of the American Chemical Society · 2024Article
- Machine Learning to Develop Peptide Catalysts-Successes, Limitations, and Opportunities.ACS central science · 2024Article
- Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes.Molecules (Basel, Switzerland) · 2023Review
- Optimizing the Local Chemical Environment on a Bifunctional Helical Peptide Scaffold Enables Enhanced Enantioselectivity and Cooperative Catalysis.Organic letters · 2022Article
- Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The combination of a peptide catalyst and a gold catalyst is presented for enantioselective addition reactions between branched aldehydes and allenamides. The two catalysts act in concert to provide γ,δ-enamide aldehydes bearing a fully substituted, benzylic stereogenic center - a structural motif common in many natural products and therapeutically active compounds - with good yields and enantioselectivities. The reaction tolerates a variety of alkyl and alkoxy substituted aldehydes and the products can be elaborated into several chiral building blocks bearing either 1,4- or 1,5- functional group relationships. Mechanistic studies showed that the conformational features of the peptide are important for both the catalytic efficiency and stereochemistry, while a balance of acid/base additives is key for ensuring formation of the desired product over undesired side reactions.
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Registered trials
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