Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H- phenothiazin-1,2, and 4-yl)ethanols and their acetates

Jürgen Brem, Sarolta Pilbák, Csaba Paizs, Gergely Bánóczi, Florin Dan Irimie, Monica Ioana Toşa, L. Poppe

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The synthesis of both enantiomers of 1-(10-ethyl-10H-phenothiazin-1,2, and 4-yl)ethanols 1a-c and their acetates via enantioselective methanolysis of the corresponding racemic esters rac 2a-c with lipase B from Candida antarctica (CaL-B) or/and by acylation of the racemic alcohols with the lipase A or lipase B from C. antarctica (CaL-A and CaL-B) is described. The absolute configuration of enantiopure 1-(10-ethyl-10H-phenothiazin-1-yl)ethyl acetate 2a was assigned as (R) by using QM/MM(hf/3-21g:uff) calculations within the CaL-B (1LBT crystal structure) enzymic environment.

Original languageEnglish
Pages (from-to)916-923
Number of pages8
JournalTetrahedron Asymmetry
Volume22
Issue number8
DOIs
Publication statusPublished - Apr 30 2011

Fingerprint

Enzyme kinetics
Lipases
Antarctic regions
Lipase
acetates
Acetates
Ethanol
ethyl alcohol
acylation
Acylation
Kinetics
Enantiomers
enantiomers
kinetics
esters
Esters
alcohols
Candida
Crystal structure
Alcohols

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H- phenothiazin-1,2, and 4-yl)ethanols and their acetates. / Brem, Jürgen; Pilbák, Sarolta; Paizs, Csaba; Bánóczi, Gergely; Irimie, Florin Dan; Toşa, Monica Ioana; Poppe, L.

In: Tetrahedron Asymmetry, Vol. 22, No. 8, 30.04.2011, p. 916-923.

Research output: Contribution to journalArticle

Brem, Jürgen ; Pilbák, Sarolta ; Paizs, Csaba ; Bánóczi, Gergely ; Irimie, Florin Dan ; Toşa, Monica Ioana ; Poppe, L. / Lipase-catalyzed kinetic resolutions of racemic 1-(10-ethyl-10H- phenothiazin-1,2, and 4-yl)ethanols and their acetates. In: Tetrahedron Asymmetry. 2011 ; Vol. 22, No. 8. pp. 916-923.
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AU - Paizs, Csaba

AU - Bánóczi, Gergely

AU - Irimie, Florin Dan

AU - Toşa, Monica Ioana

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