145968-48-5Relevant academic research and scientific papers
Asymmetric Microbial Reduction of Tetralones
Begue, Jean-Pierre,Cerceau, Claude,Dogbeavou, Anukwadey,Mathe, Laurence,Sicsic, Sames
, p. 3141 - 3144 (2007/10/02)
The reduction of α- and β-tetralones and of 4-substituted-α-tetralones with Sporobolomyces pararoseus and Rhodotorula rubra is described.Both strains were grown in well aerated fermentors, in some cases improving the conversion yields up to 100percent, and modifying the known selectivity of the reductions performed with S. pararoseus.All the reductions performed with R. rubra are enantioselective giving rise to (S)-alcohols, but they are weakly influenced by substituents at the 4-position.With this strain (S)-β-tetralol could be obtained with 90percent ee and 100percent conversion yield.Reductions performed with S. pararoseus are not enantioselective giving rise to (S)- and (R)-alcohols indicating the possible action of two reductases.These two reductases are strongly influenced by substituents at the 4-position, allowing only anti entry of the hydride, giving rise to cis-alcohols. cis-(1R,4R)-4-Methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthol 12 could be obtained enantiomerically pure with an excellent conversion yield.The crystal structure of the Mosher ester derivative of compound 12 is described.
