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Updated: May 1, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Dynamic kinetic resolution of dehydrocoronamic acid
David A Chaplin1, Martin E Fox, Sebastian H B Kroll
1Chirotech Technology Centre, Dr Reddy's Laboratories EU Ltd., Unit 410 Cambridge Science Park, Milton Road, Cambridge, CB4 0PE, UK. mfox@drreddys.com.
Dehydrocoronamic acid racemization is achieved via N-acyl dehydration to azlactones. This process, combined with enzymatic resolution, enables dynamic kinetic resolution for enantiomer production.
Area of Science:
- Organic Chemistry
- Biocatalysis
Background:
- Dehydrocoronamic acid is a key intermediate.
- Racemization is crucial for accessing enantiopure compounds.
Purpose of the Study:
- To develop a method for efficient racemization of dehydrocoronamic acid.
- To achieve dynamic kinetic resolution for enantioselective synthesis.
Main Methods:
- Dehydration of N-acyl dehydrocoronamic acid derivatives to azlactones.
- Facile racemization of azlactones.
- Enzymatic resolution of N-trifluoroacetyl derivative.
Main Results:
- Azlactones readily undergo racemization.
- Dynamic kinetic resolution successfully converted racemate to a single enantiomer.
Conclusions:
- Azlactone formation is an effective strategy for dehydrocoronamic acid racemization.
- The combined approach enables efficient enantioselective synthesis.
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