Epi-cinchona based thiourea organocatalyst family as an efficient asymmetric Michael addition promoter: Enantioselective conjugate addition of nitroalkanes to chalcones and α,β-unsaturated N-acylpyrroles

Benedek Vakulya, Szilárd Varga, Tibor Soós

Research output: Contribution to journalArticle

139 Citations (Scopus)

Abstract

(Chemical Equation Presented) A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the conjugate additions with high enantioselectivities and chemical yields. The extension of this methodology was further explored to encompass α,β-unsaturated N-acylpyrroles, as a chalcone mimic. Functionally, the N-acylpyrrole moiety in the adduct acts as an ester surrogate; therefore, it can easily be transformed to various valuable and biologically relevant compounds. This approach allowed the concise stereoselective synthesis of (R)-rolipram.

Original languageEnglish
Pages (from-to)3475-3480
Number of pages6
JournalJournal of Organic Chemistry
Volume73
Issue number9
DOIs
Publication statusPublished - May 2 2008

ASJC Scopus subject areas

  • Organic Chemistry

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