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Synthesis of Allenyl Esters by Horner-Wadsworth-Emmons Reactions of Ketenes Mediated by Isopropylmagnesium Bromide

Shigeki Sano*, Tomoya Matsumoto, Teppei Yano, Munehisa Toguchi, Michiyasu Nakao

*Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan, Email: ssanotokushima-u.ac.jp

S. Sano, T. Matsumoto, T. Yano, M. Toguchi, M. Nakao, Synlett, 2015, 26, 2135-2138.

DOI: 10.1055/s-0034-1378803


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Abstract

A magnesium(II)-mediated Horner-Wadsworth-Emmons reaction of bis(2,2,2-trifluoroethyl)phosphonoacetate derivatives with disubstituted ketenes enables the synthesis of tri- and tetrasubstituted allenes including α-fluorinated allenyl carboxamides.

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Key Words

Wittig-Horner reaction, allenes, ketenes, Grignard reagents


ID: J60-Y2015