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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 3.0).

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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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