Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-09-15 DOI:10.1016/j.tetasy.2017.08.002

Aoife M. Foley , Declan P. Gavin , Ilona Joniec , Anita R. Maguire

引用次数: 5

Abstract

By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.

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酰基的变化对脂肪酶介导的2-苯烷醇分离效率和选择性的影响

通过调节酰基的位阻性质来控制分解的效率和选择性，利用短链酰基通过脂肪酶催化水解制备了2-苯基-1-丙醇1a，其e值高达66 (ee高达95%)。在优化条件下，2-苯基丁醇1b同样可以被分解(高达86% ee)，而在这些条件下，更具立体要求的3-甲基-2-苯基丁醇1c的酯被证明是耐酶解的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.