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

Barbara Kovács, Enikő Forró, Ferenc Fülöp

Research output: Contribution to journalArticle

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Abstract

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%).

Original languageEnglish
Pages (from-to)6873-6877
Number of pages5
JournalTetrahedron
Volume74
Issue number48
DOIs
Publication statusPublished - Nov 29 2018

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Keywords

  • CAL-B
  • Kinetic resolution
  • Substrate specificity
  • ß-carboline

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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