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Molecules 2014, 19(5), 6309-6329; doi:10.3390/molecules19056309

Bifunctionalized Allenes. Part XIII. A Convenient and Efficient Method for Regioselective Synthesis of Phosphorylated α-Hydroxyallenes with Protected and Unprotected Hydroxy Group

Department of Organic Chemistry & Technology, Faculty of Natural Sciences, Konstantin Preslavsky University of Shumen, 115, Universitetska Str., BG-9712 Shumen, Bulgaria
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Received: 9 April 2014 / Revised: 1 May 2014 / Accepted: 5 May 2014 / Published: 16 May 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

The paper describes a convenient and efficient method for regioselective synthesis of phosphorylated α-hydroxyallenes using an atom economical [2,3]-sigmatropic rearrangement of intermediate propargyl phosphites or phosphinites. These can be readily prepared via reaction of protected alkynols with dimethyl chlorophosphite or chlorodiphenyl phosphine respectively in the presence of a base.
Keywords: synthesis; hydroxy group protection; [2,3]-sigmatropic rearrangement; phosphorylated α-hydroxyallenes synthesis; hydroxy group protection; [2,3]-sigmatropic rearrangement; phosphorylated α-hydroxyallenes
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Ismailov, I.E.; Ivanov, I.K.; Christov, V.C. Bifunctionalized Allenes. Part XIII. A Convenient and Efficient Method for Regioselective Synthesis of Phosphorylated α-Hydroxyallenes with Protected and Unprotected Hydroxy Group. Molecules 2014, 19, 6309-6329.

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