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

Autor:	Frank Laib, Syed J. Mahmood, M. Mahmun Hossain, Mary Rose Atuu
Rok vydání:	2004
Předmět:	Ester derivatives biology Organic Chemistry Ethyl ester Tropic acid Catalysis Kinetic resolution Inorganic Chemistry Acylation chemistry.chemical_compound chemistry biology.protein Vinyl acetate Organic chemistry Methanol Physical and Theoretical Chemistry Lipase
Zdroj:	Tetrahedron: Asymmetry. 15:3091-3101
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2004.08.013
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7aea58f1b7d2bb86c481cc6d59f6425a https://doi.org/10.1016/j.tetasy.2004.08.013 Zobrazit plný text záznamu Full Text from ScienceDirect