ArticleACS catalysis
Enantioselective Addition of Bromonitromethane to Aliphatic
Article in ACS catalysis. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 29 citations in OpenAlex.
- Computational Identification of Potential Organocatalysts (CIPOC) Reveals a 2-aminoDMAP/Urea Catalyst Superior to Its Thiourea Analogue.Journal of the American Chemical Society · 2025Article
- 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
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- 1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.Synthesis · 2017Article
- A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.Chemical science · 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
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
This report details the enantioselective synthesis of β-amino-α-bromo nitroalkanes with β-alkyl substituents, using homogeneous catalysis to prepare either antipode. Use of a bifunctional Brønsted base/acid catalyst allows equal access to either enantiomer of the products, enabling the use of Umpolung Amide Synthesis (UmAS) to prepare the corresponding L- or D-α-amino amide bearing alkyl side chains - overall, in only 4 steps from aldehyde. The approach also addresses an underlying incompatibility between bromonitromethane and solid hydroxide bases.
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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.