Acc Chem Res. 2000 Oct;33(10):715-27.

Dynamic thermodynamic resolution: control of enantioselectivity through diastereomeric equilibration.

Beak P, Anderson DR, Curtis MD, Laumer JM, Pippel DJ, Weisenburger GA.

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Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.

Abstract

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 on 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.

PMID:: 11041836; [PubMed - indexed for MEDLINE]

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