ArticleChemical science
Enantioselective Synthesis of D-α-Amino Amides from Aliphatic Aldehydes.
Article in Chemical science. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Backbone-Determined Antiarrhythmic Structure-Activity Relationships for a Mirror Image, Oligomeric Depsipeptide Natural Product.Journal of medicinal chemistry · 2024Article
- Enantioselective organocatalytic strategies to access noncanonical α-amino acids.Chemical science · 2024Review
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- Nitroalkanes as thioacyl equivalents to access thioamides and thiopeptides.Nature communications · 2023Article
- Enantioselective Synthesis ofOrganic letters · 2023Article
- Preparation ofJournal of the American Chemical Society · 2022Article
- Resolving Bromonitromethane Sourcing by Synthesis: Preparation at the Decagram Scale.The Journal of organic chemistry · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- An Optimized Synthesis of Fmoc-l-Homopropargylglycine-OH.The Journal of organic chemistry · 2022Article
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- Tandem Alkylation-Second-Order Asymmetric Transformation Protocol for the Preparation of Phenylalanine-Type Tailor-Made α-Amino Acids.ACS omega · 2018Article
- A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.Chemical science · 2017Article
- Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.The Journal of organic chemistry · 2017Article
- Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.Journal of the American Chemical Society · 2016Article
- Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer.Chemical communications (Cambridge, England) · 2016Article
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2 authors.
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Abstract
Peptides consisting of D-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of D-amino amides most often involves approaches based on enzymatic resolution or fractional recrystallization of their diastereomeric amine salts, techniques that produce an equal amount of the L-amino acid. Enantioselective synthesis, however, promises selective and general access to a specific α-amino amide, and may enable efficient peptide synthesis regardless of the availability of the corresponding α-amino acid. This report describes the use of a cinchona alkaloid-catalyzed aza-Henry reaction using bromonitromethane, and the integration of its product with Umpolung Amide Synthesis. The result is a straightforward 3-step protocol beginning from aliphatic aldehydes that provides homologated peptides bearing an aliphatic side chain at the resulting D-α-amino amide.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.