Azlactone Dynamic Kinetic Resolution Catalyzed by Chiral Phosphoric Acids: Mechanism and Origin of the Enantioselectivity

Download
Favorite this paper
How to cite this paper?
Details
  • Presentation type: Apresentação de Pôster / Poster Communications
  • Track: Homogeneous/Heterogeneous Catalysis
  • Keywords: Azlactone; Dynamic Kinetic Resolution; Enantioselectivity;

Authors:

  • 1 Universidade Federal de Juiz de Fora
  • 2 Department of Chemistry / Interdisciplinary Nanoscience Center / Aarhus University

Azlactone Dynamic Kinetic Resolution Catalyzed by Chiral Phosphoric Acids: Mechanism and Origin of the Enantioselectivity

Pedro Pôssa de Castro

Universidade Federal de Juiz de Fora

Abstract

- Density functional theory calculations and control experiments.
Insights on the mechanism and origin of enantioselectivity in phosphoric acid catalyzed dynamic kinetic resolution of azlactones.
Münchnone-type intermediate as the key species involved in the isomerization of azlactone rings.
Prediction of the enantioselectivity in a diversity of reaction conditions, including alcoholysis and aminolysis.

Questions (1 topic)

Share your ideas or questions with the authors!

Did you know that the greatest stimulus in scientific and cultural development is curiosity? Leave your questions or suggestions to the author!

Sign in to interact

Have a question or suggestion? Share your feedback with the authors!

Author

Pedro Pôssa de Castro

Obrigado Josefredo! As barreiras para a etapa de abertura (as conformações mais estáveis) foram todas abaixo de 20 kcal/mol para todos os pontos avaliados. No caso específico da reação mostrada em maiores detalhes, as barreiras foram de 16.9 kcal/mol para o enantiômero minoritário e de 14.8 kcal/mol para o majoritário (DDG = 2.1 kcal/mol).