<abstract xmlns="http://www.w3.org/1999/xhtml"><p>An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the mediated 3-(dimethoxyphosphanyloxy)-alk-4-ynoates is described. Alkyl 5-(dimethoxyphosphoryl)-alka-3,4-dienoates can be readily prepared via reaction of alkyl 3-hydroxy-alk-4-ynoates with dimethylchlorophosphite in the presence of a base. Alkyl 3-hydroxy-alk-4-ynoates were prepared by reaction of the metallated acetylenes with commercialy available alkyl 3-oxoalkanoates.</p></abstract>

An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the mediated 3-(dimethoxyphosphanyloxy)-alk-4-ynoates is described. Alkyl 5-(dimethoxyphosphoryl)-alka-3,4-dienoates can be readily prepared via reaction of alkyl 3-hydroxy-alk-4-ynoates with dimethylchlorophosphite in the presence of a base. Alkyl 3-hydroxy-alk-4-ynoates were prepared by reaction of the metallated acetylenes with commercialy available alkyl 3-oxoalkanoates.

Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates

Department of Chemistry, Faculty of Natural Sciences

Konstantin Preslavsky University of Shumen

Acta Scientifica Naturalis

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

An efficient method for regioselective synthesis of 5-(dimethoxyphosphoryl)-allenecarboxylates by an atom economical [2,3]-sigmatropic rearrangement of the...

Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates

Published Online: Dec 08, 2020

Page range: 1 - 10

DOI: https://doi.org/10.2478/asn-2020-0029

Keywords
alkyl 3-hydroxy-alk-4-ynoates, 5-(dimethoxyphosphoryl)-allenecarboxylates, [2,3]-sigmatropic rearrangement, regioselective synthesis

© 2020 Hasan H. Hasanov et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Bifunctionalized Allenes. Part XXIII. An Efficient Method for Regioselective Synthesis of 5-Phosphorylated Allenecarboxylates

Published Online: Dec 08, 2020

Page range: 1 - 10

DOI: https://doi.org/10.2478/asn-2020-0029

Keywordsalkyl 3-hydroxy-alk-4-ynoates, 5-(dimethoxyphosphoryl)-allenecarboxylates, [2,3]-sigmatropic rearrangement, regioselective synthesis

© 2020 Hasan H. Hasanov et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Keywords
alkyl 3-hydroxy-alk-4-ynoates, 5-(dimethoxyphosphoryl)-allenecarboxylates, [2,3]-sigmatropic rearrangement, regioselective synthesis