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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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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58744

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: http://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.