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Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.

Research paper by Peter S PS Hynes, Daniela D Stranges, Paul A PA Stupple, Antonio A Guarna, Darren J DJ Dixon

Indexed on: 05 May '07Published on: 05 May '07Published in: Organic Letters



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.