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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.