Candida antarctica lipase B catalysed kinetic resolution of 1,2,3,4-tetrahydro-β-carbolines: Substrate specificity

被引：8

作者：

Kovacs, Barbara ^{[1
]}

Forro, Eniko ^{[1
]}

Fulop, Ferenc ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, Eotvos U 6, H-6720 Szeged, Hungary

来源：

TETRAHEDRON | 2018年 / 74卷 / 48期

关键词：

beta-carboline; Substrate specificity; Kinetic resolution; CAL-B; TETRAHYDRO-BETA-CARBOLINE; STRICTOSIDINE; ALKALOIDS; ACYLATION;

D O I：

10.1016/j.tet.2018.10.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the frame of substrate specificity, CAL-B-catalysed asymmetric N-alkoxycarbonylations of 1-substituted tetrahydro-beta-carbolines (Me, Et, Pr, iPr) have been studied. High enantioselectivities (>200) were observed, when alkoxycarbonylation of racemic compounds (+/-)-1,35,7 were performed in DIPE in the presence of phenyl allyl carbonate and Et3N at 60 degrees C using ultrasound shaking method. The reaction time increased considerably with increasing substituent size on C1; however, the isopropyl-substituted compound proved to be too bulky for the optimum activity of CAL-B. The (R)-carbamate enantiomers were hydrolysed using Pd-2(dba)(3 center dot)CHCI3 and the enantiomers of the free amines were obtained with excellent ee (>99%). (C) 2018 Published by Elsevier Ltd.

引用

页码：6873 / 6877

页数：5

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