Stereoselective Barbier-Type Allylation Reaction of Trifluoromethyl Aldimines

Stereoselective Barbier-Type Allylation Reaction of Trifluoromethyl Aldimines

Trifluoromethyl aldimines could react, under Barbier conditions in the presence of activated zinc, in DMF at room temperature or in THF at reflux, with various allyl bromides to provide the corresponding homoallylamines. Secondary homoallyl trifluoromethylamines were stereoselectively obtained from...

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Veröffentlicht in:Journal of organic chemistry 2003-08, Vol.68 (16), p.6444-6446
Hauptverfasser: Legros, Julien, Meyer, Franck, Coliboeuf, Matthieu, Crousse, Benoît, Bonnet-Delpon, Danièle, Bégué, Jean-Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Allyl Compounds - chemical synthesis
Chemistry
Exact sciences and technology
Imines - chemistry
Indicators and Reagents
Indium - chemistry
Magnesium - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
Zinc - chemistry
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Zusammenfassung:Trifluoromethyl aldimines could react, under Barbier conditions in the presence of activated zinc, in DMF at room temperature or in THF at reflux, with various allyl bromides to provide the corresponding homoallylamines. Secondary homoallyl trifluoromethylamines were stereoselectively obtained from the optically active aldimine 12 with an excellent diastereoisomeric excess (98%).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034205c