Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, alpha-chlorination, hydride reduction and ring closure was developed. In addition, novel primary beta-iodo amines were obtained by regioselecti...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 9; no. 20; pp. 7217 - 7223
Main Authors Kenis, Sara, D'hooghe, Matthias, Verniest, Guido, Vinh Duc Nguyen, Tuyet Anh Dang Thi, Tuyen Van Nguyen, De Kimpe, Norbert
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2011
Subjects
Acetone - analogs & derivatives
Acetone - chemistry
Alkylation
Aziridines - chemical synthesis
Chemistry
Chemistry, Organic
Fluorine Compounds - chemical synthesis
Methylation
Molecular Structure
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
TRANSFORMATION
AMINATION
ASYMMETRIC-SYNTHESIS
REAGENTS
AMINES
RING-OPENING REACTIONS
STEREOSELECTIVE-SYNTHESIS
AZIRIDINES
FLUORINE CHEMISTRY
Online AccessGet full text

Cover

More Information
Summary:An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, alpha-chlorination, hydride reduction and ring closure was developed. In addition, novel primary beta-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel alpha-CF3-beta-phenylethylamines upon treatment with lithium diphenylcuprate.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob05813d