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Stereoselective Barbier-type allylation reaction of trifluoromethyl aldimines
Authors:Legros Julien  Meyer Franck  Coliboeuf Matthieu  Crousse Benoît  Bonnet-Delpon Danièle  Bégué Jean-Pierre
Affiliation:BioCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Chatenay-Malabry 92296 Cedex, France.
Abstract: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%).
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