Intramolecular stereoselective protonation of aldehyde-derived enolates

Research output: Contribution to journalArticleResearchpeer review

Authors

  • Anastasie Kena-diba
  • Claudia Noll
  • Michael Richter
  • Marc Timo Gieseler
  • Markus Kalesse

External Research Organisations

  • Helmholtz Centre for Infection Research (HZI)
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Details

Original languageEnglish
Pages (from-to)8367-8369
Number of pages3
JournalAngewandte Chemie - International Edition
Volume49
Issue number45
Publication statusPublished - 2 Nov 2010
Externally publishedYes

Abstract

Picking sides: Asymmetric protonation of the titled compounds poses a most significant challenge and has been addressed by taking advantage of internal protonation and subsequent hemiacetal formation to avoid epimerization (see scheme). The substrates employed in these transformations can be easily accessed through a sequence of vinylogous aldol reactions with subsequent conjugate reductions.

Keywords

    Asymmetric catalysis, Natural products, Organocatalysis, Protonation, Reduction

ASJC Scopus subject areas

Cite this

Intramolecular stereoselective protonation of aldehyde-derived enolates. / Kena-diba, Anastasie; Noll, Claudia; Richter, Michael et al.
In: Angewandte Chemie - International Edition, Vol. 49, No. 45, 02.11.2010, p. 8367-8369.

Research output: Contribution to journalArticleResearchpeer review

Kena-diba A, Noll C, Richter M, Gieseler MT, Kalesse M. Intramolecular stereoselective protonation of aldehyde-derived enolates. Angewandte Chemie - International Edition. 2010 Nov 2;49(45):8367-8369. doi: 10.1002/anie.201004619
Kena-diba, Anastasie ; Noll, Claudia ; Richter, Michael et al. / Intramolecular stereoselective protonation of aldehyde-derived enolates. In: Angewandte Chemie - International Edition. 2010 ; Vol. 49, No. 45. pp. 8367-8369.
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