Asymmetric catalysis

Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions

Richard D. Carpenter, James C. Fettinger, Kit Lam, Mark J. Kurth

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Control of stereochemistry is achieved using two TentaGel-bound di-tert-butoxyprotected hydroxyprolyl-threonine catalysts (see picture, sphere represents TentaGel). These catalysts mediate asymmetric tandem enamine/Michael reactions with high enantioselectivity and complete diastereoselectivity; the choice of catalyst depends on the desired absolute configuration. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)6407-6410
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number34
DOIs
StatePublished - Aug 11 2008

Fingerprint

Catalysis
Resins
Derivatives
Catalysts
Threonine
Stereochemistry
Enantioselectivity
Tentagel resin

Keywords

  • Asymmetric catalysis
  • Heterocycles
  • Heterogeneous catalysis
  • Solid-phase synthesis
  • Stereoselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Asymmetric catalysis : Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions. / Carpenter, Richard D.; Fettinger, James C.; Lam, Kit; Kurth, Mark J.

In: Angewandte Chemie - International Edition, Vol. 47, No. 34, 11.08.2008, p. 6407-6410.

Research output: Contribution to journalArticle

Carpenter, Richard D. ; Fettinger, James C. ; Lam, Kit ; Kurth, Mark J. / Asymmetric catalysis : Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 34. pp. 6407-6410.
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