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Synthesis 1993; 1993(10): 977-980
DOI: 10.1055/s-1993-25984
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One-Step Synthesis of Tertiary α-Amino Ketones and α-Amino Esters From Amines and Diazocarbonyl Compounds

F. G. West* , Kevin W. Glaeske, B. N. Naidu
  • *Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
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Publication Date:
29 April 2002 (online)

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Diazoketones and diazoesters react with tertiary amines in the presence of copper powder to form transient ammonium ylides. These ylides undergo facile [1,2]-shift from N to C (Stevens rearrangement) of the best migrating group. Overall, α-substituted α-amino ketones or α-amino esters are formed in one step from simple reactants.