Rapid Asymmetric Synthesis of Highly Functionalized Indanols via a 
Michael/Henry Organocascade with Submol% Squaramide Catalyst Loadings

Loh, Charles C. J.; Chauhan, Pankaj; Hack, Daniel; Lehmann, Christian W.; Enders, Dieter

doi:10.1002/adsc.201400499

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Rapid Asymmetric Synthesis of Highly Functionalized Indanols via a Michael/Henry Organocascade with Submol% Squaramide Catalyst Loadings

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

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Citation

Loh, C. C. J., Chauhan, P., Hack, D., Lehmann, C. W., & Enders, D. (2014). Rapid Asymmetric Synthesis of Highly Functionalized Indanols via a Michael/Henry Organocascade with Submol% Squaramide Catalyst Loadings. Advanced Synthesis & Catalysis, 356(14-15), 3181-3186. doi:10.1002/adsc.201400499.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-BF60-B

Abstract

An expedient asymmetric synthesis of
polyfunctionalized indanols bearing four contiguous
stereogenic centres, including a quarternary centre
through the use of sub-mol% amounts of a squaramide
catalyst within minutes is presented. A gramscale
experiment of this Michael/Henry organcascade
pushes the frontier of catalyst loading of organocascades
down to only 0.1 mol%, attaining
a TON of up to 910.