Ketoreductase-Catalyzed Access to Axially Chiral 2,6-Disubstituted Spiro[3.3]heptane Derivatives

• Published in: Organic letters Vol. 24; no. 18; pp. 3431 - 3434
• Main Authors: O’Dowd, Hardwin, Manske, Jenna L., Freedman, Seth A., Cochran, John E.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.05.2022; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; CYCLOBUTANES; RESOLUTION; SCAFFOLDS

The desymmetrization of a prochiral 6-oxaspiro[3.3]­heptane-2-carboxylic acid derivative via biocatalytic ketoreductase-mediated reduction has provided access to both enantiomers in high ee. The axially chiral alcohol was converted to the corresponding ester alcohol, amino acid, and amino alcohol bu...