Industrially Viable Syntheses of Highly Enantiomerically Enriched 1-Aryl Alcohols via Asymmetric Hydrogenation

Autor:	David A. Chaplin, Graham Meek, Julian P. Henschke, Antonio Zanotti-Gerosa, Paul H. Moran, James A. Ramsden, Paul H. M. Harrison, Christopher J. Pilkington, Ian C. Lennon, Simon Watkins
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Ketone Aryl Organic Chemistry High selectivity Asymmetric hydrogenation Enantioselective synthesis Catalysis chemistry.chemical_compound chemistry Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Acetophenone
Zdroj:	Organic Process Research & Development. 7:89-94
ISSN:	1520-586X 1083-6160
Popis:	The practicalities of the asymmetric hydrogenation of acetophenone derivatives are addressed. The catalysts used, derived from the precatalysts [(xylylPhanePhos)RuCl2(DPEN)] (S)-(R,R)-1 and (R)-(S,S)-1, were shown to possess very high reactivity. 4‘-Fluoroacetophenone was hydrogenated at a molar substrate-to-catalyst ratio (S/C) of 100,000 with complete conversion effected in as little as 80 min (average turnover ∼1200 min-1, peak turnover ∼2500 min-1). The catalysts are tolerant of a range of commercial grade substrates, in most cases a S/C of 5000−10000 was achieved without the need to purify the ketone. Using precatalyst 1 enantioselectivities of 95 → 99% ee were achieved. The high selectivity and catalyst activity, plus the simplicity of the process, offers significant advantages over other enantioselective ketone reductions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cd22ea17094717642c3a6ed2287e21de https://doi.org/10.1021/op025585r Zobrazit plný text záznamu