Synthesis of optically active 3-substituted-10-alkyl-10H-PHENOTHIAZINE-5-OXIDE (cas 1207-71-2)s by enantioselective biotransformations

Add time:07/19/2019    Source:sciencedirect.com

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.

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