Synthesis of 1-Alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening toward Diverse α-(Trifluoromethyl)Amines via Intermediate Azetidinium Salts

被引：53

作者：

Kenis, Sara ^{[1
]}

D'hooghe, Matthias ^{[1
]}

Verniest, Guido ^{[1
,3
]}

Tuyet Anh Dang Thi ^{[2
]}

Chinh Pham The ^{[2
]}

Tuyen Van Nguyen ^{[2
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium

[2] Vietnam Acad Sci & Technol, Inst Chem, Hanoi, Vietnam

[3] Vrije Universiteit Brussel, Fac Sci & Bioengn Sci, Dept Chem, B-1050 Brussels, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 14期

关键词：

STRAIGHTFORWARD SYNTHESIS; ACETYLENIC SULFONES; FLUORINE; AZIRIDINES; CHEMISTRY; ACID; REGIOSELECTIVITY; PHARMACEUTICALS; QUINOLIZIDINES; PYRROLIZIDINES;

D O I：

10.1021/jo300694y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed staffing from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.

引用

页码：5982 / 5992

页数：11

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