alpha,beta-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water

A.J. Boersma, B.L. Feringa, G. Roelfes

Research output: Contribution to journalArticleAcademicpeer-review

113 Citations (Scopus)

Abstract

alpha,beta-Unsaturated 2-acyl imidazoles are a novel and practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. The Diels-Alder products are obtained with very high diastereoselectivities and enantioselectivities in the range of 83-98%. The catalytic reaction was performed on a 1.0 mmol scale, and the imidazole auxiliary was removed readily.

Original languageEnglish
Pages (from-to)3647-3650
Number of pages4
JournalOrganic letters
Volume9
Issue number18
DOIs
Publication statusPublished - 30-Aug-2007

Keywords

  • ARTIFICIAL METALLOENZYMES
  • ENANTIOSELECTIVE CATALYSIS
  • TRIFLATE COMPLEXES
  • BIOTIN-AVIDIN
  • HYDROGENATION
  • PROTEIN
  • DESIGN

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