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2
Regioselective oxidative cleavage of benzylidene acetals: synthesis of alpha- and beta-benzoyloxy carboxylic acids.苄叉缩醛的区域选择性氧化裂解：α-和β-苯甲酰氧基羧酸的合成
Angew Chem Int Ed Engl. 2010;49(4):804-7. doi: 10.1002/anie.200905952.
3
Enantioselective copper-catalyzed propargylic amination.对映选择性铜催化的炔丙基胺化反应
Angew Chem Int Ed Engl. 2008;47(20):3777-80. doi: 10.1002/anie.200705264.
4
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J Comb Chem. 2007 Nov-Dec;9(6):1188-92. doi: 10.1021/cc700127f. Epub 2007 Sep 27.

在中性条件下使用铜（I）促进消除炔丙酯来拆分羧酸。

Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions.

机构信息

Chemical Methodologies and Library Development Center, 2034 Becker Drive, University of Kansas, Lawrence, Kansas 66047-3761, United States.

出版信息

J Org Chem. 2011 May 20;76(10):4168-72. doi: 10.1021/jo200433w. Epub 2011 Apr 14.

DOI:10.1021/jo200433w
PMID:21491889
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3691273/
Abstract

A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ≥94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.

摘要

介绍了一种拆分羧酸的光学方法。外消旋羧酸与手性末端炔丙醇缩合得到可分离的非对映异构体酯。通过色谱分离，然后在甲醇中加热各个非对映异构体，并加入催化量的卤化亚铜（I），可以以良好的收率和≥94%的对映体过量值再生羧酸。该方法特别适用于与传统酯水解不兼容的羧酸的拆分。