Efficient dynamic kinetic resolution of secondary alcohols with a novel tetrafluorosuccinato ruthenium complex

S.F.G.M. Nispen, van, J. Buijtenen, van, J.A.J.M. Vekemans, J. Meuldijk, L.A. Hulshof

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

21 Citaten (Scopus)

Samenvatting

Dynamic kinetic resolution (DKR) of a series of secondary alcohols has been conducted with a novel dinuclear ruthenium complex, bearing tetrafluorosuccinate and (rac)-BINAP ligands as the racemization catalyst. Novozym 435 has been used as the enzyme, and isopropyl butyrate as the acyl donor. Five substrates underwent DKR successfully: an aliphatic and an aromatic secondary alcohol, an aromatic alcohol with an electron-withdrawing substituent on the phenyl ring, an aromatic alcohol bearing an electron-donating substituent on the ring and a heteroaromatic secondary alcohol. The catalyst performed optimally at 70 °C. Typically the reaction reached complete conversion within 1 day with 0.1 mol % of racemization catalyst relative to the substrate. The addition of the ketone corresponding to the substrate stabilizes the active Ru complex and, therefore, increases the rate of the reaction.
Originele taal-2Engels
Pagina's (van-tot)2299-2305
TijdschriftTetrahedron: Asymmetry
Volume17
Nummer van het tijdschrift15
DOI's
StatusGepubliceerd - 2006

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