Base-Catalyzed Isomerization of 2-Isoxazolines Enables a Two-Step Enantioselective Synthesis of beta-Hydroxynitriles from Enals

[摘要]：The asymmetric synthesis of beta-hydroxynitriles remains a challenge in organic synthesis. Herein we report a convenient synthesis of beta-hydroxynitriles from enantiomerically enriched 3-unsubstituted 2-isoxazolines via a base-catalyzed ring-opening reaction that takes place without loss of enantiopurity. In combination with organocatalytic enantioselective synthesis of 3-unsubstituted 2-isoxazolines, the ring-opening enables a short 2-step synthesis of beta-hydroxynitriles from alpha,beta-unsaturated aldehydes in high enantiomeric purity.

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