Efficient lipase-catalysed route for the kinetic resolution of salsolidine and its ß-carboline analogue

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI:10.1016/j.tetasy.2017.10.019

Barbara Kovács, Rita Megyesi, Enikő Forró, Ferenc Fülöp

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引用次数: 8

Abstract

Racemic 1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1 and 1-methyl-1,2,3,4-tetrahydro-ß-carboline 3 were resolved through lipase-catalysed asymmetric acylation on the secondary amino group. High enantioselectivities (E >200) were observed when the acylation of racemic 1 was performed with phenyl allyl carbonate in the presence of Candida rugosa lipase in toluene at 40 °C or with Candida antarctica lipase B in tert-butyl methyl ether at 50 °C. Excellent enantioselectivity (E >200) characterised the CAL-B-catalysed acylation of racemic 3 with phenyl allyl carbonate in the presence of triethylamine in tert-butyl methyl ether at 50 °C. The product (R)-carbamates (ee >97%) were hydrolysed into the corresponding (R)-enantiomers of the free amines 1 and 3 (ee = 99%) with the use of Pd₂(dba)₃·CHCl₃ catalyst.

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高效脂肪酶催化的salsolidine及其ß-carboline类似物动力学分解途径

外消旋的1-甲基-6,7-二甲氧基-1,2,3,4-四氢异喹啉1和1-甲基-1,2,3,4-四氢-carboline 3通过脂肪酶催化在二级氨基上的不对称酰化分解。当外消旋体1与碳酸苯烯丙酯在甲苯中有念珠菌脂肪酶存在(温度为40 °C)或与南极念珠菌脂肪酶B在叔丁基甲基醚中(温度为50 °C)进行酰化时，观察到较高的对映选择性(E >200)。优异的对映选择性(E >200)表征了cal -b催化的外消旋3与碳酸苯烯丙酯在三乙胺存在下在50 °C的叔丁基甲基醚中的酰化反应。产物(R)-氨基甲酸酯(ee >97%)在Pd2(dba)3·CHCl3催化剂的催化下水解成相应的游离胺1和3 (ee = 99%)的(R)-对映体。

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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.