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Molecules 2010, 15(4), 2551-2563; doi:10.3390/molecules15042551

Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes

, , , , , *,  and *
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China
* Authors to whom correspondence should be addressed.
Received: 9 December 2009 / Revised: 3 March 2010 / Accepted: 19 March 2010 / Published: 12 April 2010
(This article belongs to the Special Issue Asymmetric Synthesis)
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To map out the efficient organocatalyst requirements in the Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes, a dozen different amino organocatalysts containing a p-toluenesulfonyl group (Ts) have been evaluated; excellent enantio-selectivities (up to er 92:8) were obtained with a primary amine-based Ts-DPEN catalyst and a plausible catalytic reaction mechanism was proposed on the basis of the experimental results.
Keywords: organocatalysis; Michael reaction; primary amine; diamine organocatalysis; Michael reaction; primary amine; diamine
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Jiang, Z.-Y.; Yang, H.-M.; Ju, Y.-D.; Li, L.; Luo, M.-X.; Lai, G.-Q.; Jiang, J.-X.; Xu, L.-W. Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes. Molecules 2010, 15, 2551-2563.

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