ArticleChemistry (Weinheim an der Bergstrasse, Germany)2023
Nms-Amides: An Amine Protecting Group with Unique Stability and Selectivity.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Unified Synthesis of Unconventional α-Polyhalogenated Amines Through Hydroaminoalkylation.Angewandte Chemie (International ed. in English) · 2026Article
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- Enhanced crystallinity of tetrahalopyridyl (THP) derivatized compounds.Chemical science · 2026Article
- Electrophilic and Radical Ability of Organic Nitrating Reagents.The Journal of organic chemistry · 2026Article
- Deprotective Functionalization: An Emerging Concept for Amine Reactivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Facile (Z)-Selective Synthesis of β,γ-Unsaturated Ketones by a Silicon-based Olefination Strategy.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Cyclobutane-Containing Tricyclic β-Lactams Based on a Saturated Scaffold Enabled by Iron-catalysed [2 + 2]-Cycloaddition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Intramolecular N-O Bond Formation for the Synthesis ofJournal of the American Chemical Society · 2025Article
- Steric Effects ofMolecules (Basel, Switzerland) · 2025Article
- Synthesis of Complex Tetracyclic Fused Scaffolds Enabled by (3 + 2) Cycloaddition.Organic letters · 2024Article
- Deprotective Functionalization: A Direct Conversion of Nms-Amides to Carboxamides Using Carboxylic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Nms-Amides: An Amine Protecting Group with Unique Stability and Selectivity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
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Authors and funding
12 authors.
Funding
Abstract
p-Toluenesulfonyl (Tosyl) and nitrobenzenesulfonyl (Nosyl) are two of the most common sulfonyl protecting groups for amines in contemporary organic synthesis. While p-toluenesulfonamides are known for their high stability/robustness, their use in multistep synthesis is plagued by difficult removal. Nitrobenzenesulfonamides, on the other hand, are easily cleaved but display limited stability to various reaction conditions. In an effort to resolve this predicament, we herein present a new sulfonamide protecting group, which we term Nms. Initially developed through in silico studies, Nms-amides overcome these previous limitations and leave no room for compromise. We have investigated the incorporation, robustness and cleavability of this group and found it to be superior to traditional sulfonamide protecting groups in a broad range of case studies.
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