The key step in the chemoenzymatic synthesis of apremilast was to produce chiral alcohol (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanol, (R)-3. Two enzymatic approaches were evaluated obtain (R)-3, one using ketoreductases and other lipases. Bioreduction 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanone (2), ketoreductase KRED‑P2-D12, led (R)-3 with 48% conversion 93% enantiom...

Continuing our research on the use of organophosphorus derivatives aziridines in asymmetric synthesis and expanding scope their applicability, chiral aziridine-phosphines obtained earlier laboratory were used as catalysts Morita–Baylis–Hillman reaction methyl vinyl ketone acrylate with various aromatic aldehydes. The desired products formed moderate to high chemical yields enantiomeric excess r...

Amino acids are important targets in the search for life beyond Earth. The types of amino acids, their relative abundances, and enantiomeric excess all serve as biosignatures. To detect such biosignatures, identification quantification individual required. Regardless analytical workflow used, it is critical to release from sample without altering molecular distributions. Subcritical water extra...

Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step ...