Journal Article Electrophilic Derivatization of Trifluoromethyl-Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring Transformations

Kurohara, Takashi  ,  Shibuya, Masatoshi  ,  Yamamoto, Yoshihiko

359 ( 8 )  , pp.1413 - 1419 , 2017-04-17 , Wiley
ISSN:1615-4150
Description
To extend the synthetic potential of trifluoromethyl-substituted semisquarate (CF3-semisquarate) previously synthesized by us as a pluripotent building block, its electrophilic derivatization was investigated. The electrophilic addition of allylic silanes and silyl enolates to CF3-semisquarate afforded the corresponding 4-hydroxycyclobutenones. Subsequent ring expansion of these products via thermolysis or oxidation using lead tetraacetate afforded trifluoromethylated bicyclo[3.2.0]heptenones or (Z)-γ-alkylidenetetronates.
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