Synthetic Strategy toward γ-Keto Nitriles and Their Biocatalytic Conversion to Asymmetric γ-Lactones

Authors

Sarah E. Franz, Armstrong Atlantic State University
Richard R. Watkins, Armstrong Atlantic State University
Laura A. Wright, Armstrong Atlantic State University
Blair A. Weaver, Armstrong Atlantic State University
Ramon C. Hartage, Armstrong Atlantic State University
Ion Ghiviriga, University of FloridaFollow
Giuseppe Gumina, Presbyterian CollegeFollow
Brent D. Feske, Armstrong Atlantic State UniversityFollow

Document Type

Article

Publication Date

6-25-2013

Publication Title

Synthesis

DOI

10.1055/s-0033-1339282

ISSN

0039-7881

Abstract

Asymmetric γ-hydroxy nitriles are valuable intermediates because hydrolysis of the nitriles can result in an intramolecular cyclization to chiral γ-lactones, which have a variety of biological uses. Starting with an assortment of different aldehydes (alkyl and aryl) a 4-step synthesis of γ-keto nitriles was developed. These prochiral substrates were then screened against a library of ketoreductases for their ability to stereoselectively reduce the carbonyl. Enzymes from the short chain dehydrogenase family showed activity and these enzymatic reactions were scaled up to produce a diverse set of chiral γ-lactones.

Recommended Citation

Franz, Sarah E., Richard R. Watkins, Laura A. Wright, Blair A. Weaver, Ramon C. Hartage, Ion Ghiviriga, Giuseppe Gumina, Brent D. Feske. 2013. "Synthetic Strategy toward γ-Keto Nitriles and Their Biocatalytic Conversion to Asymmetric γ-Lactones." Synthesis, 45 (15): 2171-2178. doi: 10.1055/s-0033-1339282 source: https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0033-1339282
https://digitalcommons.georgiasouthern.edu/chem-facpubs/126