Enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes

Leandro Piovan; Monica D Pasquini; Leandro H Andrade

doi:10.3390/molecules16098098

Enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl)phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes

Molecules. 2011 Sep 20;16(9):8098-109. doi: 10.3390/molecules16098098.

Authors

Leandro Piovan¹, Monica D Pasquini, Leandro H Andrade

Affiliation

¹ Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, São Paulo, Brazil.

Abstract

The enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl) phenylcarbamate via lipase-catalyzed transesterification reaction was studied. We investigated several reaction conditions and the carbamate was resolved by Candida antarctica lipase B (CAL-B), leading to the optically pure (R)- and (S)-enantiomers. The enzymatic process showed excellent enantioselectivity (E > 200). (R)- and (S)-tert-butyl 2-(1-hydroxyethyl)phenylcarbamate were easily transformed into the corresponding (R)- and (S)-1-(2-aminophenyl)ethanols.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biocatalysis
Candida / enzymology*
Esterification
Fungal Proteins / chemistry*
Kinetics
Lipase / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Organometallic Compounds / chemical synthesis*
Organoselenium Compounds / chemical synthesis*
Oxidation-Reduction
Phenylcarbamates / chemical synthesis*
Phenylcarbamates / chemistry
Solvents
Stereoisomerism
Tellurium / chemistry*

Substances

Fungal Proteins
Organometallic Compounds
Organoselenium Compounds
Phenylcarbamates
Solvents
tert-butyl 2-(1-hydroxyethyl)phenylcarbamate
Lipase
lipase B, Candida antarctica
Tellurium