Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones |
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Authors: | Hynes Peter S Stranges Daniela Stupple Paul A Guarna Antonio Dixon Darren J |
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Affiliation: | School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK. |
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Abstract: | 5-Aryl-1,3-dioxolan-4-one heterocycles derived from mandelic acid derivatives and hexafluoroacetone have been identified as new and effective pro-nucleophiles in highly diastereo- and enantioselective Michael addition reactions to nitro olefins catalyzed by bifunctional epi-9-amino-9-deoxy cinchona alkaloid derivatives. Diastereoselectivities up to 98% and enantioselectivities up to 89% for a range of nitro olefins and 5-aryl-1,3-dioxolan-4-ones under mild reaction conditions are reported. |
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