Recent advances in enzymatic and chemical deracemisation of racemic compounds
Authors:
- Michał RachwalskiMichał Rachwalski
- Niek VermueNVNiek Vermue
- Floris P. J. T. RutjesFloris P. J. T. Rutjes
Open Access
- 1 January 2013
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 42 (24) , 9268-82
Abstract
Deracemisation of racemic compounds is still the most important strategy to produce optically pure compounds despite many recent advances in asymmetric synthesis. Especially deracemisation approaches that give rise to single enantiomers are preferred, which can be achieved either by invoking organocatalysts, metal complexes or enzymes - leading to dynamic kinetic resolution - or by applying other deracemisation techniques based on stereoinversion or enantioconvergence. In this tutorial review, we will provide an overview of new, recently developed approaches that lead to the important goal of creating organic compounds of single chirality.Keywords
This publication has 40 references indexed in Scilit:
- Catalytic Dynamic Kinetic Resolutions with N‐Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β‐LactonesAngewandte Chemie International Edition, 2012
- Nonenzymatic Dynamic Kinetic Resolution of α‐(Arylthio)‐ and α‐(Alkylthio)alkanoic AcidsAngewandte Chemie International Edition, 2011
- Dynamic Kinetic Resolution of Azlactones Catalyzed by Chiral Brønsted AcidsOrganic Letters, 2010
- Highly Diastereo- and Enantioselective Synthesis of Monodifferentiated syn-1,2-Diol Derivatives through Asymmetric Transfer Hydrogenation via Dynamic Kinetic ResolutionOrganic Letters, 2010
- Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenationTetrahedron: Asymmetry, 2010
- Desymmetrization of meso-1,2-Diols via the Dynamic Kinetic Resolution of Its MonodichloroacetatesThe Journal of Organic Chemistry, 2010
- Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and AminesEuropean Journal of Organic Chemistry, 2010
- Benzotetramisole-Catalyzed Dynamic Kinetic Resolution of AzlactonesOrganic Letters, 2010
- Bifunctional transition metal-based molecular catalysts for asymmetric synthesesOrganic & Biomolecular Chemistry, 2005
- Non-Sequential Processes for the Transformation of a Racemate into a Single Stereoisomeric Product: Proposal for Stereochemical ClassificationChemistry – A European Journal, 2001