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

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...

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Bibliographic Details
Published in:Organic letters 2022-05, Vol.24 (18), p.3431-3434
Main Authors: O’Dowd, Hardwin, Manske, Jenna L., Freedman, Seth A., Cochran, John E.
Format: Article
Language:English
Subjects:
Alcohols
Biocatalysis
Carboxylic Acids - chemistry
Heptanes
Stereoisomerism
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Summary: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 building blocks while high enantiopurity was maintained.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01378