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Synthesis 2014; 46(21): 2917-2926
DOI: 10.1055/s-0034-1378498
DOI: 10.1055/s-0034-1378498
paper
Copper(I) Iodide Mediated Synthesis of Carbohydrate-Based Terminal Allenes by ATA Reaction
Weitere Informationen
Publikationsverlauf
Received: 27. Mai 2014
Accepted after revision: 20. Juni 2014
Publikationsdatum:
17. Juli 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201421/lookinside/thumbnails/10.1055-s-0034-1378498-1.jpg)
Abstract
We have demonstrated two improved methods for the synthesis of carbohydrate-based terminal allenes from propargyl or homopropargyl glycosides. The reaction of propargyl or homopropargyl glycosides with paraformaldehyde (2.5 equiv) in the presence of copper(I) iodide (10 mol%) and diisopropylamine (1.8 equiv) or copper(I) iodide (50 mol%) and dicyclohexylamine (1.8 equiv) produces sugar-linked terminal allenes in 50–79% yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For selected reviews, see:
For reviews see:
For a review, see:
For selected recent reports, see:
For recent reviews or highlights on the synthesis of allenes, see: