4.3 Review

Dynamic Kinetic Resolution of Racemic Allylic Alcohols via Hydrolase-Metal Combo Catalysis: An Effective Method for the Synthesis of Optically Active Compounds

Journal

CHEMISTRY LETTERS
Volume 43, Issue 6, Pages 746-754

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.140223

Keywords

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (Japan)
  2. Asahi Glass Foundation (Japan)
  3. Grants-in-Aid for Scientific Research [26670002] Funding Source: KAKEN

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This review focuses on the dynamic kinetic resolution (DKR) of racemic allylic alcohols to produce allylic esters in high chemical and optical yields, which was achieved by combining hydrolase-catalyzed kinetic resolution and in situ racemization of the remaining less reactive enantiomers. Two classes of racemization catalysts, e.g., Ru complexes and oxovanadium compounds, are mainly discussed. Typical examples of DKR are shown along with their application in the concise syntheses of optically active compounds as valuable synthetic intermediates. The domino process integrating DKR with the active use of the installed acyl moiety for subsequent intramolecular cyclization is also discussed, which has great potential for the asymmetric syntheses of optically active fused cyclic molecules possessing multiple stereogenic centers.

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