Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.
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.
Hynes
Peter S
PS
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Stranges
Daniela
D
Stupple
Paul A
PA
Guarna
Antonio
A
Dixon
Darren J
DJ