Self-association free bifunctional thiourea organocatalysts: synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones?

Organic & Biomolecular Chemistry Pub Date: 2011-12-08 DOI: 10.1039/C1OB06629C

Abstract

Concentration-independent high enantioselectivity in the dynamic kinetic resolution (DKR) of racemic azlactones affording chiral α-aminoesters has been achieved using self-association free thiourea-based dimeric cinchona alkaloid organocatalysts. Detailed experimental studies and single crystal X-ray analysis confirmed that these bifunctional organocatalysts I do not form H-bonded self-aggregates in either solution or solid state.

Graphical abstract: Self-association free bifunctional thiourea organocatalysts: synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones
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