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 the optically active aldimine 12 with an excellent diastereoisomeric excess (98%).
Legros
Julien
J
BioCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Châtenay-Malabry 92296 Cedex, France.
Meyer
Franck
F
Coliboeuf
Matthieu
M
Crousse
Benoît
B
Bonnet-Delpon
Danièle
D
Bégué
Jean-Pierre
JP
D000498:Allyl Compounds / Q000138:chemical synthesis; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents; D007204:Indium / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000498:Allyl Compounds; D007097:Imines; D007202:Indicators and Reagents; D007204:Indium; D008274:Magnesium; D015032:Zinc