Rapid Identification of a Scalable Catalyst for the Asymmetric Hydrogenation of a Sterically Demanding Aryl Enamide

Autor: Harrie Straatman, Jeroen A. F. Boogers, Laurent Lefort, André H.M. de Vries, Johannes G. de Vries, John Janssen, Robert Jan Vijn, Thijs Kuilman
Přispěvatelé: Stratingh Institute of Chemistry, Synthetic Organic Chemistry
Jazyk: angličtina
Rok vydání: 2010
Předmět:
Zdroj: Organic Process Research & Development, 14(3), 568-573. AMER CHEMICAL SOC INC
Popis: High throughput screening was used to find a cost-effective and scalable catalyst for the asymmetric hydrogenation of a sterically demanding enamide as an intermediate towards a new potent melanocortin receptor agonist useful in the treatment of obesity. Lessons drawn from the testing of a first library of 96 chiral monodentate phosphoramidites led to the design of a second focused library of 16 chiral ligands, allowing the discovery of a new efficient catalyst. This catalyst was based on rhodium and a bulky monodentate phosphite ligand. The catalyst was scaled up and used in the kilogram production of the desired bulky chiral amide.
Databáze: OpenAIRE