Next Article in Journal
Solid-Phase Synthesis of a New Diphosphate 5-Aminoimidazole-4-carboxamide Riboside (AICAR) Derivative and Studies toward Cyclic AICAR Diphosphate Ribose
Next Article in Special Issue
A QM/MM–Based Computational Investigation on the Catalytic Mechanism of Saccharopine Reductase
Previous Article in Journal
Design and Synthesis of New N-(5-Trifluoromethyl)-1H-1,2,4-triazol-3-yl Benzenesulfonamides as Possible Antimalarial Prototypes
Previous Article in Special Issue
Optimized Enzymatic Synthesis of Hesperidin Fatty Acid Esters in a Two-Phase System Containing Ionic Liquid
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2011, 16(9), 8098-8109; doi:10.3390/molecules16098098

Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes

Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, São Paulo, Brazil
*
Author to whom correspondence should be addressed.
Received: 19 August 2011 / Revised: 14 September 2011 / Accepted: 15 September 2011 / Published: 20 September 2011
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Download PDF [552 KB, uploaded 18 June 2014]   |  

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.
Keywords: alcohols; carbamates; lipases; kinetic resolution; enatiopure alcohols; carbamates; lipases; kinetic resolution; enatiopure
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Piovan, L.; Pasquini, M.D.; Andrade, L.H. Enzymatic Kinetic Resolution of tert-Butyl 2-(1-Hydroxyethyl)phenylcarbamate, A Key Intermediate to Chiral Organoselenanes and Organotelluranes. Molecules 2011, 16, 8098-8109.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top