98516-82-6

Upstream product

• 3979-14-4 tropic acid ethyl ester 
• 108-24-7 acetic anhydride 
• 103-82-2 phenylacetic acid 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 

Relevant academic research and scientific papers

Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides

Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.

Kinetic resolution of tropic acid ethyl ester and its derivatives by lipase PS

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.