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.
Organocatalytic Diastereo- and Enantioselective Michael Addition Reactions of 5-Aryl-1,3-dioxolan-4-ones / HYNES P. S; STRANGES D; STUPPLE P. A; A. GUARNA; DIXON D. J. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 9:(2007), pp. 2107-2110. [10.1021/ol070532l]
Organocatalytic Diastereo- and Enantioselective Michael Addition Reactions of 5-Aryl-1,3-dioxolan-4-ones
GUARNA, ANTONIO;
2007
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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