Enantiodivergence in alkylation of 1-(6-methoxynaphth-2-yl)ethyl acetate by potassium dimethyl malonate catalyzed by chiral palladium-DUPHOS complex |
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Authors: | Martine Assié Abdelkrim Meddour Jean-Claude Fiaud Jean-Yves Legros |
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Institution: | 1. Laboratoire de Catalyse Moléculaire, ICMMO, Université de Paris-Sud, 91405 Orsay cedex, France;2. Laboratoire de RMN en milieu orienté, ICMMO, Université de Paris-Sud, 91405 Orsay cedex, France |
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Abstract: | Alkylation of racemic 1-(6-methoxynaphth-2-yl)ethyl acetate by potassium dimethyl malonate catalyzed by a chiral palladium-DUPHOS complex afforded the substitution product with 87% ee, along with 6-methoxy-2-vinylnaphthalene that arose from an elimination process, in a 43/57 substitution/elimination ratio. The reaction performed on a mixture of quasi-enantiomeric substrates provided insight into the stereochemical course of the reaction, establishing that—for a given enantiomer of the catalyst, one enantiomer of the substrate afforded mainly the substitution product whereas the other enantiomer underwent elimination. |
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