Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 15, Pages 2075-2079Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200606178
Keywords
dimethylzinc; enantioselective; ephedrine; ethyl iodoacetate; Reformatsky reaction
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The admission of air in the reaction mixture of imine, ethyl iodoacetate and dimethylzinc, in the presence of 20-30 mol % of inexpensive and commercially available N-methylephedrine as the chiral ligand, promoted the Reformatsky reaction, without the need for other metals or catalysts. Excellent yields (up to 92 %) and enantioselectivities (83-94 %) were obtained for the tested substrates. The reaction shows a broad scope, and all the imines are prepared in situ, using Me2Zn as the dehydrating agent.
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