Effect of alkaloids on the activity and selectivity of Candida rugosa lipase in the kinetic resolution of 2-hydroxymethyl-1-phenylthioferrocene with planar chirality

The use of the o-(4-chlorobenzoyl) hydroquinine as an additive in the enzymatic transesterification in the presence of Candida rugosa lipase (CRL) of a planar chiral molecule, such as 2-hydroxymethyl-1-phenylthioferrocene, shows a large enhancement of the reactivity and selectivity of this lipase towards this primary alcohol. An E-value of 143 could be reached at 53% conversion with vinyl acetate as the acylating agent in toluene.

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(SFc)-2-Hydroxymethyl-1-phenylthio-ferroceneC17H16FeOSEe = 99%[α]D = −56.2 (c 1, CH2Cl2)Absolute configuration: (SFc)Source of chirality: asymmetric synthesis