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

被引：6
|
作者：
Kurohara, Takashi [1 ]
Shibuya, Masatoshi [1 ]
Yamamoto, Yoshihiko [1 ]
机构：
[1] Nagoya Univ, Grad Sch Pharmaceut Sci, Dept Basic Med Sci, Nagoya, Aichi 4648601, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 08期
关键词：
fluorine; cyclobutenedione; ring expansion; bicycloalkenone; tetronate; FLUORINE; CHEMISTRY;
D O I：
10.1002/adsc.201601297
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
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)-gamma-alkylidenetetronates.
引用
收藏
页码：1413 / 1419
页数：7
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