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Synfacts 2010(2): 0230-0230  
DOI: 10.1055/s-0029-1219129
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrization of meso-1,3-Diones Catalyzed by Chiral Phosphoric Acids

Contributor(s): Benjamin List, Steffen Müller
K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, T. Akiyama*
Gakushuin University, Tokyo and Rikkyo University, Tokyo, Japan
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

TRIP was found to be a suitable catalyst to efficiently promote the desymmetrization of 1,3-diones by means of an intramolecular aldol-condensation reaction. The desired cyclohexenones were obtained in high yields and enantioselectivities of up to 97:3 er. In contrast to the classical two-step desymmetrization-dehydration sequence (e.g., catalyzed by proline), the substrate-catalyst interaction is based on hydrogen bonding instead of covalent interactions. A plausible transition state, based on quantum chemical calculation, is provided.