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

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
› Author Affiliations
Further Information

Publication History

Received: 03 June 2015

Accepted after revision: 17 June 2015

Publication Date:
10 August 2015 (online)


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