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CC BY 4.0 · Synlett
DOI: 10.1055/a-2681-2944
Letter

Synthesis of Allenyl Esters by Horner–Wadsworth–Emmons-Type Reactions of Methyl 2-[Bis(benzylthio)phosphoryl]acetate and Ketenes Using Grignard Reagents

Michiyasu Nakao
1   Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima, Japan
,
Masakazu Tabaru
2   Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, Japan
,
Ayato Imai
2   Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, Japan
,
Syuji Kitaike
2   Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, Japan
,
Shigeki Sano
1   Graduate School of Pharmaceutical Sciences, The University of Tokushima, Tokushima, Japan
› Institutsangaben
Gefördert durch: Japan Society for the Promotion of Science JP20K06966,JP23K06026
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Methyl 2-[bis(benzylthio)phosphoryl]acetate and its analogues have proven to be efficient Horner–Wadsworth–Emmons (HWE)-type reagents for synthesizing conjugated allenyl esters and their analogues through reactions with disubstituted ketenes using Grignard reagents. A series of HWE-type reagents containing the bis(benzylthio)phosphoryl group showed better reactivity than corresponding HWE reagents, where two phosphorus–sulfur bonds were substituted with phosphorus–oxygen bonds.



Publikationsverlauf

Eingereicht: 20. Mai 2025

Angenommen nach Revision: 08. August 2025

Accepted Manuscript online:
11. August 2025

© . The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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