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

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

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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
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.

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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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