Resolution of racemic 1-hydroxyalkylferrocenes by lipase B from Candida Antarctica

The resolution of 1-hydroxyethylferrocene, (+/-)-1, 1-hydroxypropylferrocene, (+/-)-2, and 1-hydroxy-2,2,2-trifluoroethylferrocene, (+/-)-4, has been achieved through stereoselective irreversible transesterification catalysed by immobilised Candida antarctica lipase in t-butyl methyl ether, resulting in the formation of the R esters possessing high enantiomeric purity. No reaction occurred with 1-hydroxy-2-methylpropylferrocene, (+/-)-3, and 1-hydroxybenzylferrocene, (+/-)-5. The same lipase catalysed efficiently the enantioselective alcoholysis of the acetates (+/-)-1a, (+/-)-2a and (+/-)-4a.