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Synfacts 2008(5): 0532-0532
DOI: 10.1055/s-2008-1072685
DOI: 10.1055/s-2008-1072685
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Mannich Reaction of Acetaldehyde
J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Further Information
Publication History
Publication Date:
23 April 2008 (online)
Significance
A proline-catalyzed Mannich reaction of acetaldehyde with N-Boc imines has been reported. The authors have suppressed some potential side reactions by using 5-10 equivalents of acetaldehyde. Acetonitrile was found to be the best solvent for this reaction. With 20 mol% of proline catalyst, moderate to good yields (23-58%) and excellent enantioselectivities (er = 98:2 to >99:1) are obtained for different aromatic and aliphatic aldehyde derived N-Boc imines.