CF3-Containing para-Quinone Methides for Organic Synthesis

被引：15

作者：

Winter, Michael ^{[1
]}

Schuetz, Roman ^{[1
]}

Eitzinger, Andreas ^{[1
]}

Ofial, Armin R. ^{[2
]}

Waser, Mario ^{[1
]}

机构：

[1] Johannes Kepler Univ Linz, Inst Organ Chem, Altenbergerstr 69, A-4040 Linz, Austria

[2] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandrstr 5-13, D-81377 Munich, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 25期

关键词：

Quinone methides; Trifluoromethylation; Electrophilicity; Kinetics; Phase-transfer catalysis; ASYMMETRIC 1,6-CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYTIC 1,6-ADDITION; NUCLEOPHILIC REACTIVITIES; SULFONIUM SALTS; ACID-ESTERS; TRIFLUOROMETHYLATION; ACCESS; SPIROCYCLOPROPANATION; COMBINATIONS;

D O I：

10.1002/ejoc.202000295

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new family of CF3-containing para-quinone methides (CF3-QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF3-containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF3-QM 2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one was determined to be -11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.

引用

页码：3812 / 3817

页数：6

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