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Electrophilic Derivatization of Trifluoromethyl-Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring TransformationsElectrophilic Derivatization of Trifluoromethyl-Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring Transformations |
"/Kurohara, Takashi/"Kurohara, Takashi ,
"/Shibuya, Masatoshi/"Shibuya, Masatoshi ,
"/Yamamoto, Yoshihiko/"Yamamoto, Yoshihiko
359
(
8
)
, pp.1413
-
1419 , 2017-04-17 , Wiley
ISSN:1615-4150
内容記述
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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