Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

Ildikó Gergely, Csaba Hegedüs, A. Szöllösy, Axel Monsees, Thomas Riermeier, J. Bakos

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Electronic and steric effects in the rhodium diphosphinite catalyzed asymmetric hydrogenation were investigated. A series of electronically and sterically modified (S)-BINOL and (S)-H8-BINOL ligands was synthesized and effects on the catalytic performance were studied. Phosphinite basicity was varied by using p-CH3O, p-CH3, p-H, p-CF 3, 3,5-(CH3)2, 3,5-(CF3) 2 substituents on the diphenylphosphine moieties. In the hydrogenation of dimethyl itaconate and methyl (Z)-α-acetamido cinnamate an increase in enantioselectivity and activity was observed with increasing phosphine basicity.

Original languageEnglish
Pages (from-to)9025-9028
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number50
DOIs
Publication statusPublished - Dec 8 2003

Fingerprint

Rhodium
phosphine
Hydrogenation
Alkalinity
Cinnamates
Ligands
Enantioselectivity
naphthol BINOL
dimethyl itaconate

Keywords

  • Asymmetric hydrogenation
  • Dimethyl itaconate
  • Diphosphinites
  • Methyl(Z)-α-acetamido cinnamate
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation. / Gergely, Ildikó; Hegedüs, Csaba; Szöllösy, A.; Monsees, Axel; Riermeier, Thomas; Bakos, J.

In: Tetrahedron Letters, Vol. 44, No. 50, 08.12.2003, p. 9025-9028.

Research output: Contribution to journalArticle

Gergely, Ildikó ; Hegedüs, Csaba ; Szöllösy, A. ; Monsees, Axel ; Riermeier, Thomas ; Bakos, J. / Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 50. pp. 9025-9028.
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AU - Monsees, Axel

AU - Riermeier, Thomas

AU - Bakos, J.

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