Organocatalytic desymmetrization of cyclic meso-anhydrides through enantioselective alcoholysis with functionalized primary nitroallylic alcohols

Yan Ming Chen, Mamatha Amireddy, Kwunmin Chen

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The direct organocatalytic desymmetrization of cyclic meso-anhydrides was achieved by alcoholysis with nitroallylic alcohols. The reaction between primary nitroallylic alcohols and cyclic meso-anhydrides catalyzed by cinchonidine derived thiourea organocatalyst II (10 mol %) proceeded smoothly. The corresponding hemiesters were obtained in high chemical yields with high to excellent levels of stereoselectivity (up to 90% yield and 99% ee). On the other hand, the reversal of enantioselectivity was observed when an amino cinchonidine derivative (III) was used as the organocatalyst under the similar reaction conditions. This demonstrated an example of activation of the nucelophilic component in the desymmetrization of cyclic meso-anhydrides.

Original languageEnglish
Pages (from-to)9064-9069
Number of pages6
JournalTetrahedron
Volume70
Issue number47
DOIs
Publication statusPublished - 2014 Nov 25

Keywords

  • Desymmetrization
  • Michael addition
  • Organocatalysis
  • Thiourea

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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