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Synfacts 2008(12): 1337-1337  
DOI: 10.1055/s-0028-1083573
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrizing Aldol Cyclodehydration

Contributor(s): Benjamin List, Corinna Reisinger
J. Zhou, V. Wakchaure, P. Kraft, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany and Givaudan Schweiz AG, Dübendorf, Switzerland
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Publication History

Publication Date:
20 November 2008 (online)

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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.