Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Mavrynsky D, Kanerva LT, Sillanpaa R, Leino R
Förläggare: INT UNION PURE APPLIED CHEMISTRY
Publiceringsår: 2011
Tidskrift: Pure and Applied Chemistry
Tidskriftsakronym: PURE APPL CHEM
Volym: 83
Nummer: 3
Artikelns första sida, sidnummer: 479
Artikelns sista sida, sidnummer: 487
Antal sidor: 9
ISSN: 0033-4545


Abstrakt

An improved gram-scale synthesis of Bn5CpRu(CO)(2)Cl is reported based on heating of pentabenzylcyclopentadiene with Ru-3(CO)(12) at 160 degrees C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted ligand precursor with hexane provided pure title compound in 77 % yield. In combination with Candida antarctica lipase B (CAL-B) (Novozym 435), this complex forms a highly active racemization catalyst for metallo enzymatic dynamic kinetic resolution (DKR) of secondary alcohols as demonstrated in the present work by converting 100 g of racemic 1-phenylethanol to (R)-1-phenylethanol in > 99 % ee and 93 % overall yield over two steps using 0.05 mol % loading of the metal catalyst and 1 mass % loading of immobilized enzyme. In addition, the synthesis and crystallographic characterization of the palladium congener Bn5CpPd(PPh3)Cl are briefly discussed.


Nyckelord

chemoenzymatic synthesis, cyclopentadienyl, dynamic kinetic resolution (DKR), Novozym, ruthenium

Senast uppdaterad 2019-06-12 vid 04:12