ArticleACS central science2016
An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed Stereodivergent Propargylation of Unprotected Aldoses.
Article in ACS central science, 2016. 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, 60 citations in OpenAlex.
- Highly Catalytic Allylation of Native Carbohydrates in Water with Indium: Kinetic, Mechanistic, and Spectroscopic Studies.Journal of the American Chemical Society · 2026Article
- Article
- Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.Molecules (Basel, Switzerland) · 2023Review
- Improved synthesis and application of conjugation-amenable polyols from d-mannose.RSC advances · 2020Article
- Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis.Journal of the American Chemical Society · 2019Article
- Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds.The Journal of organic chemistry · 2019Article
- Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.ChemCatChem · 2019Article
- Thermal, Spectroscopic, and Crystallographic Analysis of Mannose-Derived Linear Polyols.Crystal growth & design · 2018Article
- Enantioselective copper catalysed, direct functionalisation of allenesChemical science · 2017Review
- Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.Angewandte Chemie (International ed. in English) · 2016Article
- C-Propargylation Overrides O-Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium-Catalyzed Transfer Hydrogenation.Angewandte Chemie (International ed. in English) · 2016Article
- Beyond Protecting Groups in Metal Catalyzed C-C Coupling: Direct Anomeric Propargylation of Aldoses.ACS central science · 2016Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We developed a copper(I)-catalyzed stereodivergent anomeric propargylation of unprotected aldoses as a facile synthetic pathway to a broad variety of sialic acid derivatives. The soft allenylcopper(I) species, catalytically generated from stable allenylboronic acid pinacolate (2), is unusually inert to protonolysis by the multiple hydroxy groups of the substrates and thereby functions as a carbon nucleophile. The key additive B(OMe)3 facilitated ring-opening of the nonelectrophilic cyclic hemiacetal forms of aldoses to the reactive aldehyde forms. The chirality of the catalyst, and not the internal stereogenic centers of substrates, predominantly controlled the stereochemistry of the propargylation step; i.e., the diastereoselectivity was switched simply by changing the catalyst chirality. This is the first nonenzyme catalyst-controlled stereodivergent C-C bond elongation at the anomeric center of unprotected aldoses, which contain multiple protic functional groups and stereogenic centers. The propargylation products can be expeditiously transformed into naturally occurring and synthetic sialic acid derivatives in a simple three-step sequence. This synthetic method, which requires no protecting groups, can be performed on a gram-scale and thus offers general and practical access to various sialic acid derivatives from unprotected aldoses.
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Registered trials
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