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Dynamic thermodynamic resolution: Control of enantioselectivity through diastereomeric equilibration

Journal

ACCOUNTS OF CHEMICAL RESEARCH
Volume 33, Issue 10, Pages 715-727

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ar000077s

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Funding

  1. NIGMS NIH HHS [GM-18874] Funding Source: Medline

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A theoretical foundation, tools for recognition:and control, and recent examples of a class of asymmetric transformation termed dynamic thermodynamic resolution are presented. Enantioselective reaction pathways that involve an induced diastereomeric equilibration to intermediates, which are configurationally stable bn the time scale of a subsequent reaction, are illustrated. Dynamic thermodynamic resolution differs from the classic, well-documented pathways of kinetic resolution and dynamic kinetic resolution in that equilibration and resolution can be operative on one system in separate controllable steps. This approach offers a high level of flexibility and provides multiple opportunities for optimization of enantioselectivity.

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