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Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence

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Dreier,  Angelika
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Blümel, M., Chauhan, P., Vermeeren, C., Dreier, A., Lehmann, C. W., & Enders, D. (2015). Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence. Synthesis, 47(22), 3618-3628. doi:10.1055/s-0035-1560072.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0029-3033-C
Abstract
The asymmetric organocatalytic one-pot Michael/Michael/ aldol reaction of trifluoromethyl-substituted 1,3-dicarbonyl compounds, nitroolefins, and 2-arylidene indandiones catalyzed sequentially by a cinchona-derived squaramide and DBU leads to spirocyclohexane-indan-1,3-diones bearing five adjacent stereogenic centers including a trifluoromethylated one in medium to very good yields and enantioselectivities, but generally in low to high diastereomeric ratios.