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Synthesis 2020; 52(06): 847-852
DOI: 10.1055/s-0039-1690730
DOI: 10.1055/s-0039-1690730
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Gram-Scale Synthesis of the Co(nmp)2 Catalyst to Prepare trans-2,5-Disubstituted Tetrahydrofurans by the Aerobic Oxidative Cyclization of Pent-4-en-1-ols
We thank the University of Western Ontario, WSS NSERC Bridge (Grant 47229) and the Natural Sciences and Engineering Research Council of Canada (NSERC) (DG RGPIN-2014-04891) for financial support. B.M. and N.A.M. thank NSERC for Vanier and CGSD Scholarships support, respectively.Weitere Informationen
Publikationsverlauf
Received: 01. September 2019
Accepted after revision: 03. Oktober 2019
Publikationsdatum:
08. Januar 2020 (online)
Abstract
Co(nmp)2 is an efficient catalyst for the aerobic oxidative cyclization of pent-4-en-1-ols to give 5-hydroxymethyl trans-tetrahydrofurans (THFs) as single diastereomers in high yield. The trans-THF pharmacophore is of interest because it is found in many biologically active natural products. The three-step synthesis of Co(nmp)2 described here gives the catalyst as a fine powder in 80–85% overall yield on 10-gram scale. The use of the catalyst in a representative oxidative cyclization is also described.
Key words
catalysis - cyclization - furans - green chemistry - heterocycles - ligands - oxygenations - stereoselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690730.
- Supporting Information
- CIF File
-
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