Process for transition metal-catalyzed asymmetric hydrogenation of acrylic acid derivatives, and a novel catalyst system for asymmetric transition metal catalysis

US7473792B2 · kind B2 · utility

Assignee

• DSM Fine Chemicals Austria NFG GmbH & Co KG · AT

Inventors

• Jeroen Antonius Franciscus Boogers · Eijsden, NL
• Ulfried Felfer · Linz, AT
• Martina Kotthaus · Linz, AT
• Andreas H. M. de Vries · Eijsden, NL
• Johannes Gerardus De Vries · Rostock, DE
• Laurent Lefort · Kaiseraugst, CH
• Gerhard Steinbauer · Ansfelden, AT

Key dates

• Filing date: Dec 5, 2005
• Grant date: Jan 6, 2009
• Expiry date: Dec 5, 2025

Classification

• Technology area (CPC B): Performing Operations; Transporting
• CPC primary: B01J2531/827
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for transition metal-catalyzed, asymmetric hydrogenation of acrylic acid derivatives of the formula (I) in which R1 is H or an optionally substituted alkyl, aryl or heteroaryl radical, R2 is an optionally substituted alkyl, aryl or heteroaryl radical, and R3 is H or a C1-C6-alkyl radical, which comprises hydrogenating compounds of the formula (I), optionally in a solvent, in the presence of one or more hydrogen donors, using a catalyst system which comprises a transition metal from the group of ruthenium, rhodium and iridium and a combination of a chiral phosphorus ligand of the formula (II) in which Cn, together with the two oxygen atoms and the phosphorus atom, forms an optionally substituted ring having from 2 to 6 carbon atoms and R4 is an optionally substituted alkyl, aryl, alkoxy or aryloxy radical or NR5R6 where R5 and R6 may each independently be H or an optionally substituted alkyl, aryl, aralkyl or alkaryl radical, or, together with the nitrogen atom, may form a ring, and an achiral phosphine ligand of the formula (III) in which R is an optionally substituted alkyl or aryl radical, to the corresponding compounds of the formula (IV) in which R1, R2 and R3 are eac…