Add time:07/12/2019         Source:sciencedirect.com

The first kinetic resolution of tropic acid ethyl ester (TAEE) with lipase PS and vinyl acetate as an acylating agent is reported. The resulting (S)-(−)-3-acetoxy tropic acid ethyl ester and (R)-(+)-tropic acid ethyl ester are produced in high yields and in excellent ee (87–94%). The method has been extended to resolve a variety of tropic acid ester derivatives. In addition, an improved method for the preparation of racemic mixtures of tropic acid ethyl ester and its derivatives from 3-hydroxy-2-phenylacrylic acid ethyl ester using NaBH4 in methanol is reported. This procedure is better than the previous ones because it is cleaner, safer and can be worked up easily. An improved method of deacylating the chiral 3-acetoxy tropic acid ethyl ester without any loss of stereochemical integrity using HCl/CH3OH is also reported.

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