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Molecules 2015, 20(4), 7263-7275; doi:10.3390/molecules20047263

Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes

Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska str., BG-9712 Shumen, Bulgaria
These authors contributed equally to this work.
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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 March 2015 / Revised: 15 April 2015 / Accepted: 17 April 2015 / Published: 21 April 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

Phosphorylated α-hydroxyallenes 1 and 2 were smoothly converted into the corresponding 2,5-dihydrofurans 3 and 4 in an 5-endo-trig cycloisomerization reaction by using 5 mol % of coinage metal salts as catalyst. Experimental conditions such as the type of the solvent, the reaction temperature, the mol % and the type of the catalyst were optimized. This mild and efficient cyclization method can be applied to dimethyl 1-hydroxyalkyl-alka-1,2-dienephosphonates 1 and 2-diphenylphosphinoyl-2,3-dien-1-ols 2ac and 3-diphenylphosphinoyl-3,4-dien-2-ols 2d,e, furnishing 3-phosphorylated 2,5-dihydrofurans 3 and 4 in very good yields. View Full-Text
Keywords: phosphorylated α-hydroxyallenes; cycloisomerization; coinage metal catalysts; 2,5-dihydrofurans phosphorylated α-hydroxyallenes; cycloisomerization; coinage metal catalysts; 2,5-dihydrofurans
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Christov, V.C.; Ismailov, I.E.; Ivanov, I.K. Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes. Molecules 2015, 20, 7263-7275.

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