Heterocycles 30: Lipase catalyzed kinetic resolution of racemic 1-(2-aryl-4-methyl-thiazol-5-yl)ethanols

Add time:08/17/2019    Source:sciencedirect.com

The lipase mediated selective O-acylation and alcoholysis of the corresponding alcohols/butanoates have been investigated for the production of both (R)- and (S)-1-(2-aryl-thiazol-5-yl)ethanols. In terms of stereoselectivity and activity, CaL-B mediated selective acylation gave similar good results (c = 50%, E »200) in comparison with CaL-A mediated alcoholysis (c = 50%, E »200). Using the sequential kinetic resolution: first a CaL-B catalyzed (R)-selective O-acylation of racemic alcohols rac-2a–d followed by a CaL-A mediated methanolysis of the previously obtained enantiomerically enriched (R)-butanoates (R)-3a–d yielded (with 39–46% yields) both enantiopure forms of the 1-(2-aryl-thiazol-5-yl)ethanols.

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