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Lipase-Palladium Co-Catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters.

Masato Oono1, Akane Yamada2, Masanari Kimura3

  • 1Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka, 565-0871, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 13, 2025
PubMed
Summary

This study introduces an improved dynamic kinetic resolution (DKR) for racemic allylic esters using a novel palladium catalyst and sodium acetate. This method efficiently produces optically active allylic alcohols with high yields and enantioselectivity.

Keywords:
allylic alcoholdynamic kinetic resolutionhydrolysislipasepalladium

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Biocatalysis

Background:

  • Dynamic kinetic resolution (DKR) combining enzymatic catalysis with in situ racemization is well-established for esterification of sec-alcohols.
  • DKR via hydrolysis of racemic esters is less explored due to limitations in effective racemization methods.
  • Racemic allylic esters present a challenging substrate class for efficient hydrolytic DKR.

Purpose of the Study:

  • To develop an enhanced hydrolytic dynamic kinetic resolution (DKR) for racemic allylic esters.
  • To identify effective racemization catalysts and conditions for accelerating the DKR process.
  • To achieve high yields and enantioselectivity in the production of optically active allylic alcohols.

Main Methods:

  • Lipase-catalyzed hydrolysis of racemic allylic esters.
  • In situ racemization using a novel palladium complex generated from the monodentate ligand P[C6H3-2,6-(OMe)2]3.
  • Acceleration of racemization using sodium acetate (NaOAc).

Main Results:

  • The developed method enables rapid DKR of racemic allylic esters within hours at 40°C.
  • High isolated yields ranging from 58% to 91% were achieved.
  • Excellent enantioselectivities were obtained, with enantiomeric excess (ee) from 93% to >99%.

Conclusions:

  • The combination of a novel palladium catalyst and NaOAc significantly enhances hydrolytic DKR of allylic esters.
  • This approach overcomes previous limitations, offering an effective and general method for producing chiral allylic alcohols.
  • The DKR process proceeds with minimal side reactions, demonstrating its practical applicability.