Stereodivergent synthesis of 3‐hydroxyprolines and 3‐hydroxypipecolic acids via ketoreductase‐catalyzed dynamic kinetic reduction
CK Prier, MMC Lo, H Li… - Advanced Synthesis & …, 2019 - Wiley Online Library
CK Prier, MMC Lo, H Li, N Yasuda
Advanced Synthesis & Catalysis, 2019•Wiley Online LibraryWe report a practical enzymatic approach for the stereoselective synthesis of hydroxylated
cyclic amino acids. Using ketoreductases, cyclic ketoesters are converted with high
diastereo‐and enantioselectivity to all isomers of 3‐hydroxyproline and 3‐hydroxypipecolic
acid via a dynamic kinetic reduction reaction. This work highlights the ability of enzymes to
provide solutions to challenges in stereoselective synthesis.
cyclic amino acids. Using ketoreductases, cyclic ketoesters are converted with high
diastereo‐and enantioselectivity to all isomers of 3‐hydroxyproline and 3‐hydroxypipecolic
acid via a dynamic kinetic reduction reaction. This work highlights the ability of enzymes to
provide solutions to challenges in stereoselective synthesis.
Abstract
We report a practical enzymatic approach for the stereoselective synthesis of hydroxylated cyclic amino acids. Using ketoreductases, cyclic ketoesters are converted with high diastereo‐ and enantioselectivity to all isomers of 3‐hydroxyproline and 3‐hydroxypipecolic acid via a dynamic kinetic reduction reaction. This work highlights the ability of enzymes to provide solutions to challenges in stereoselective synthesis.
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