Synlett 2015; 26(15): 2135-2138
DOI: 10.1055/s-0034-1378803
letter
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Shigeki Sano*

    Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   eMail: ssano@tokushima-u.ac.jp
  • Tomoya Matsumoto

    Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   eMail: ssano@tokushima-u.ac.jp
  • Teppei Yano

    Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   eMail: ssano@tokushima-u.ac.jp
  • Munehisa Toguchi

    Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   eMail: ssano@tokushima-u.ac.jp
  • Michiyasu Nakao

    Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   eMail: ssano@tokushima-u.ac.jp
Weitere Informationen

Publikationsverlauf

Received: 03. Juni 2015

Accepted after revision: 17. Juni 2015

Publikationsdatum:
10. August 2015 (online)


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Abstract

The synthesis of conjugated allenyl esters (tri-substituted allenes) was achieved by magnesium(II)-mediated Horner–Wadsworth–Emmons reaction of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate with disubstituted ketenes. In addition, a novel access to α-fluorinated allenyl carboxamides (tetrasubstituted allenes) is presented.

Supporting Information