Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides
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Date
2021-12-15
Publication Type
Journal Article
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yes
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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 gamma,delta-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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published
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Journal / series
Volume
27 (70)
Pages / Article No.
17559 - 17564
Publisher
Wiley-VCH
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Date collected
Date created
Subject
asymmetric catalysis; enamides; fully substituted stereogenic centers; gold; peptides
Organisational unit
03940 - Wennemers, Helma / Wennemers, Helma
Notes
Funding
862081 - Cell-Like"Molecular Assembly Lines": Programmable and Self-Regulating Reactors as Game-Changers in Chemical Synthesis (EC)
188729 - Bioinspirierte Asymmetrische Katalyse (Fortsetzung 2020) (SNF)
188729 - Bioinspirierte Asymmetrische Katalyse (Fortsetzung 2020) (SNF)