Loading…
Chemoenzymatic Sequential Multistep One-Pot Reaction for the Synthesis of (1S,2R)‑1-(Methoxycarbonyl)cyclohex-4-ene-2-carboxylic Acid with Recombinant Pig Liver Esterase
In this work, the development of a chemoenzymatic process for the production of (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid by ECS-PLE06 (recombinant pig liver esterase) is presented. Herein an optimized esterification protocol, starting from the economically favored meso-anhydride 1...
Saved in:
Published in: | Organic process research & development 2015-12, Vol.19 (12), p.2034-2038 |
---|---|
Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Summary: | In this work, the development of a chemoenzymatic process for the production of (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid by ECS-PLE06 (recombinant pig liver esterase) is presented. Herein an optimized esterification protocol, starting from the economically favored meso-anhydride 1b, was established and combined with the highly selective ECS-PLE06-catalyzed desymmetrization reaction. Both reactions proceed under mild reaction conditions, and the excellent selectivity of ECS-PLE06 results in an enantiomeric excess of ≥99.5% ee. Furthermore, the presented one-pot synthesis facilitates higher isolated yields of up to 84% in comparison to the classical two-step synthesis route (70% isolated yield), which requires more expensive starting materials and two separate workup steps. |
---|---|
ISSN: | 1083-6160 1520-586X |
DOI: | 10.1021/acs.oprd.5b00294 |