Palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-, benzothiophene- and indole-based substrates by dimethyl malonate anion |
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| Authors: | Gaëlle Primault Jean-Claude Fiaud |
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| Institution: | Laboratoire de Catalyse Moléculaire associé au C.N.R.S., UMR C8075, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bâtiment 420, Université de Paris-Sud, F91405 Orsay Cedex, France |
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| Abstract: | The palladium-catalyzed benzylic-like nucleophilic substitution of acetates derived from benzofuran, benzothiophene and indole was investigated. The asymmetric substitution on racemic 1-(2-benzofuryl)ethyl acetate gave disappointing results, but the substitution product was obtained in 98% ee from (S)-1-(2-benzofuryl)ethyl acetate with overall retention of configuration. |
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| Keywords: | Palladium Benzylic-like nucleophilic substitution C-C bond formation Benzofuran Benzothiophene Indole |
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