ChemInform Abstract: Synthesis of Enantiopure 3,6,7,8-Tetrahydrochromeno[7,8-d]imidazoles via Asymmetric Ketone Hydrogenation in the Presence of RuCl2[Xyl-P-Phos][DAIPEN]

Autor:	Hans Christof Holst, Ulrike Nettekoven, Vittoria Chiesa, Andreas Palmer, Jacques Le Paih, Antonio Zanotti-Gerosa
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Ketone Enantiopure drug chemistry Base (chemistry) Yield (chemistry) Asymmetric hydrogenation General Medicine Enantiomer Medicinal chemistry Stoichiometry Catalysis
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
Popis:	The asymmetric hydrogenation of complex heterocyclic ketones 1 in the presence of the novel catalyst RuCl2[(S)-Xyl-P-Phos][(S)-DAIPEN] and a base afforded the corresponding alcohols 2 in good enantiomeric purity. The outcome of the reaction depended on the substitution pattern of the ketone and the stoichiometry of the base. After optimization of the reaction conditions, the pure alcohols 2a and 2b were isolated in good yield (>70%) and enantiomeric purity (>93% ee) and used as key intermediates for the synthesis of the pharmaceutically active 3,6,7,8-tetrahydrochromeno[7,8-d]imidazoles 3a and 3b.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8cd77105a9824894fa0d77be20e9c83c https://doi.org/10.1002/chin.200911134 Zobrazit plný text záznamu Plný text