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Synfacts 2008(12): 1337-1337
DOI: 10.1055/s-0028-1083573
DOI: 10.1055/s-0028-1083573
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Desymmetrizing Aldol Cyclodehydration
J. Zhou, V. Wakchaure, P. Kraft, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany and Givaudan Schweiz AG, Dübendorf, Switzerland
Further Information
Publication History
Publication Date:
20 November 2008 (online)

Significance
A highly enantioselective desymmetrizing intramolecular aldol condensation reaction of 4-substituted 2,6-heptanediones 1 has been established to furnish 5-substituted 3-methyl-2-cyclohexene-1-ones 3. Quinine-derived primary amine 2a in combination with acetic acid proved to be the ideal catalytic system for the desired transformation. The use of its pseudoenantiomeric analogue 2b derived from quinidine gives access to the opposite product enantiomer in equally high enantioselectivity.