Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles†
AbstractA two-step stereoselective chemoenzymatic synthesis of optically active α-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of α-, β-, and γ-chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells screened (baker’s yeast, Kluyveromyces marxianus CBS 6556, Saccharomyces cerevisiae CBS 7336, Lactobacillus reuteri DSM 20016), baker’s yeast was the one providing the best yields and the highest enantiomeric ratios (up to 95:5 er) in the bioreduction of the above ketones. The obtained optically active chlorohydrins could be almost quantitatively cyclized in a basic medium into the corresponding α-aryl-substituted cyclic ethers without any erosion of their enantiomeric integrity. In this respect, valuable, chiral non-racemic functionalized oxygen containing heterocycles (e.g., (S)-styrene oxide, (S)-2-phenyloxetane, (S)-2-phenyltetrahydrofuran), amenable to be further elaborated on, can be smoothly and successfully generated from their prochiral precursors. View Full-Text
- Supplementary File 1:
Supplementary (PDF, 192 KB)
Share & Cite This Article
Vitale, P.; Digeo, A.; Perna, F.M.; Agrimi, G.; Salomone, A.; Scilimati, A.; Cardellicchio, C.; Capriati, V. Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles. Catalysts 2017, 7, 37.
Vitale P, Digeo A, Perna FM, Agrimi G, Salomone A, Scilimati A, Cardellicchio C, Capriati V. Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles. Catalysts. 2017; 7(2):37.Chicago/Turabian Style
Vitale, Paola; Digeo, Antonia; Perna, Filippo M.; Agrimi, Gennaro; Salomone, Antonio; Scilimati, Antonio; Cardellicchio, Cosimo; Capriati, Vito. 2017. "Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles." Catalysts 7, no. 2: 37.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.