Electrophilic Derivatization of Trifluoromethyl‐Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring Transformations | Zendy

Kurohara Takashi | Zendy; Shibuya Masatoshi | Zendy; Yamamoto Yoshihiko | Zendy

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Electrophilic Derivatization of Trifluoromethyl‐Substituted Semisquarate Using Unsaturated Organosilanes and Subsequent Ring Transformations

Author(s) -

Kurohara Takashi,

Shibuya Masatoshi,

Yamamoto Yoshihiko

Publication year - 2017

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201601297

Subject(s) - chemistry , electrophile , silylation , derivatization , trifluoromethyl , silanes , allylic rearrangement , thermal decomposition , organic chemistry , electrophilic fluorination , ring (chemistry) , medicinal chemistry , silane , catalysis , alkyl , high performance liquid chromatography

To extend the synthetic potential of trifluoromethyl‐substituted semisquarate (CF 3 ‐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 CF 3 ‐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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