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

Ildikó Gergely, Csaba Hegedüs, Áron Szöllosy, Axel Monsees, Thomas Riermeier, József Bakos

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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

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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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