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Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio- and diastereoselective Michael addition reactions |
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| Authors: | Alistair J.M. Farley Pavol Jakubec Anna M. Goldys Darren J. Dixon |
| Affiliation: | 1. The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;2. Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovakia |
| Abstract: | Bifunctional iminophosphorane (BIMP) organocatalysts catalyze the enantio- and diastereoselective Michael additions of high pKa cyclic malonamate ester pro-nucleophiles to nitroalkenes with reactivity profiles of up to 3 orders of magnitude greater than tertiary amine bifunctional Brønsted base/(thio)urea organocatalysts. The unrivalled performance of the BIMPs allows reaction times of challenging reactions to be slashed from weeks to minutes and has enabled new flow chemistry applications using polystyrene-supported versions contained within a flow reactor. |
| Keywords: | Asymmetric organocatalysis Nitroolefin Michael addition Superbase BIMP Nakadomarin A Continuous flow |
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