Synthesis of optically active 3-substituted-10-alkyl-10H-phenothiazine-5-oxides by enantioselective biotransformations

Monica Toşa, Csaba Paizs, Cornelia Majdik, L. Novák, P. Kolonits, Florin Dan Irimie, L. Poppe

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A series of racemic 10-alkyl-3-formyl-10H-phenothiazine-5-oxides (±)-2a-h were subjected to biotransformation with baker's yeast resulting in optically active aldehydes (+)-2a-h and alcohols (-)-3a-h in moderate enantiomeric excess. The racemic 10-alkyl-3-hydroxymethyl-10H-phenothiazine-5-oxides (±)-3a-h and 3-acetoxymethyl-10-alkyl-10H-phenothiazine-5-oxides (±)-4a-h obtained from the racemic aldehydes (±)-2a-h were also tested in enantioselective lipase-catalyzed acetylations and alcoholysis reactions. The highest enantiomeric purities were achieved by a Novozyme 435-catalyzed acetylation-ethanolysis sequence, leading to optically active alcohols (-)-3a-h in 83-92% e.e. A novel NMR method using enantiopure dibenzoyl tartaric acid as chiral additive was developed for determination of the enantiomeric composition of the optically active products.

Original languageEnglish
Pages (from-to)211-221
Number of pages11
JournalTetrahedron Asymmetry
Volume13
Issue number2
DOIs
Publication statusPublished - Feb 28 2002

Fingerprint

phenothiazines
Biotransformation
Oxides
acetylation
Acetylation
Aldehydes
aldehydes
oxides
alcohols
Alcohols
synthesis
yeast
Lipases
Lipase
Yeast
Saccharomyces cerevisiae
purity
Nuclear magnetic resonance
nuclear magnetic resonance
acids

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of optically active 3-substituted-10-alkyl-10H-phenothiazine-5-oxides by enantioselective biotransformations. / Toşa, Monica; Paizs, Csaba; Majdik, Cornelia; Novák, L.; Kolonits, P.; Irimie, Florin Dan; Poppe, L.

In: Tetrahedron Asymmetry, Vol. 13, No. 2, 28.02.2002, p. 211-221.

Research output: Contribution to journalArticle

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