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

In the frame of substrate specificity, CAL-B-catalysed asymmetric N-alkoxycarbonylations of 1-substituted tetrahydro-ß-carbolines (Me, Et, Pr, iPr) have been studied. High enantioselectivities (>200) were observed, when alkoxycarbonylation of racemic compounds (±)-1,3,5,7 were performed in DIPE i...

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Bibliographic Details
Published in:Tetrahedron 2018-11, Vol.74 (48), p.6873-6877
Main Authors: Kovács, Barbara, Forró, Enikő, Fülöp, Ferenc
Format: Article
Language:English
Subjects:
CAL-B
Kinetic resolution
Substrate specificity
ß-carboline
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Summary:In the frame of substrate specificity, CAL-B-catalysed asymmetric N-alkoxycarbonylations of 1-substituted tetrahydro-ß-carbolines (Me, Et, Pr, iPr) have been studied. High enantioselectivities (>200) were observed, when alkoxycarbonylation of racemic compounds (±)-1,3,5,7 were performed in DIPE in the presence of phenyl allyl carbonate and Et3N at 60 °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 Pd2(dba)3.CHCl3 and the enantiomers of the free amines were obtained with excellent ee (>99%). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.10.034