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

Peter S. Hynes, Daniela Stranges, Paul A. Stupple, Antonio Guarna, Darren J. Dixon

Research output: Contribution to journalArticleResearchpeer-review

78 Citations (Scopus)

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-amino9-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.

Original languageEnglish
Pages (from-to)2107-2110
Number of pages4
JournalOrganic Letters
Volume9
Issue number11
DOIs
Publication statusPublished - 24 May 2007
Externally publishedYes

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