Iridium-Catalyzed Enantioselective Hydrogenation of Terminal Alkenes

Autor: Andreas Pfaltz, Esther Hörmann, Sebastian P. Smidt, Frederik Menges, Steven McIntyre
Rok vydání: 2005
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 347:282-288
ISSN: 1615-4150
DOI: 10.1002/adsc.200404256
Popis: Iridium complexes derived from chiral P,N ligands are efficient catalysts for the enantioselective hydrogenation of 2-aryl-substituted terminal alkenes. Using 0.1-1 mol % of catalyst at room temperature and ambient hydrogen pressure, high enantioselectivities (88-94% ee), full conversions after short reaction times and essentially quantitative yields were obtained for a range of differently substituted 2-arylalkenes. Among six iridium complexes that were tested, the most selective catalyst was a complex with a phosphinite-oxazoline ligand derived from threonine (Ir-ThrePHOX). In contrast to the hydrogenation of trisubstituted alkenes, a strong pressure effect was observed for this class of substrates. Lowering the hydrogen pressure from 50 to 1 bar resulted in a strong increase of the ee values.
Databáze: OpenAIRE