Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL‐B

• Published in: European Journal of Organic Chemistry
• Main Authors: Päiviö, Mari, Mavrynsky, Denys, Leino, Reko, Kanerva, Liisa T.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2011
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/ejoc.201001703; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201001703; http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201001703/fullpdf

Abstract The substrate scope in the dynamic kinetic resolution ofsecondary alcohols was studied by using 31 structurallydifferent alcohols and isopropenyl acetate in the presence ofdicarbonylchlorido(pentabenzylcyclopentadienyl)rutheniumand Candida antarctica lipase B (Novozym 435, CAL‐B) in toluene. The enzyme and the ruthenium complex were shown to function in a highly compatible manner allowing the conversion of the racemic alcohols into the ( R )‐acetates in practically theoretical yields and, in most cases, ee values exceeding 99 %. The results are fully comparable to those published previously by using earlier reported, state‐of‐the‐art ruthenium‐based catalysts for the alcohol racemization. A clear benefit of the dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium system, when compared to other (cyclopentadienyl)ruthenium racemization catalysts, is its simple and cost‐efficient preparation.