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Organic & Biomolecular Chemistry

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Paper

Org. Biomol. Chem., 2007, 5, 816 - 821, DOI: 10.1039/b616504d


Organocatalytic enantioselective indole alkylations of ,-unsaturated ketones

Wei Chen, Wei Du, Lei Yue, Rui Li, Yong Wu, Li-Sheng Ding and Ying-Chun Chen


The C3-selective enantioselective Michael-type Friedel–Crafts alkylations of indoles with nonchelating ,-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to –20 °C. Moderate to good ee (47–89%) has been achieved.

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