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

页码：1413 / 1419

页数：7

共 28 条

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