Abstract
Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their division into three main groups: (1) cyclodextrins promoting asymmetric and stereospecific catalysis in water; (2) cyclodextrins’ complexes with transition metals as asymmetric and stereospecific catalysts; and (3) cyclodextrins’ non-metallic derivatives as asymmetric and stereospecific catalysts. The scope of this review is to systematize existing information on the contribution of cyclodextrins to asymmetric and stereospecific synthesis and, thus, to facilitate further development in this direction.
Highlights
Cyclodextrins (CDs) have long been known to be good contributors to the development of catalytic processes
We propose the following division of the topics according to the structure and functionality of the cyclodextrin-based catalysts: 1) cyclodextrins’ complexes with transition metals as asymmetric and stereospecific catalysts; 2) cyclodextrins’ non-metallic derivatives as asymmetric and stereospecific catalysts; 3) cyclodextrins promoting asymmetric and stereospecific catalysis in water
The role of CDs in the enantioselectivity of the reactions with the participation of these complexes can be explained by preorganization of the substrates in the hydrophobic cavity and specific exposure of the reaction affected groups to the metal-catalytic part of the complex
Summary
Cyclodextrins (CDs) have long been known to be good contributors to the development of catalytic processes. Cyclodextrins have been successfully used as powerful resolving agents for racemic mixtures [6], as well as separating agents in gas chromatographic chiral resolution of enantiomers [7,8,9] It is a well-known fact that the formation of an inclusion complex between the β-CD unit of a catalytic system and a substrate leads to an increase of the local concentration of the latter and immobilizes it near the catalytically-active center. Cyclodextrins from the first two groups, as a part of the metal-containing or non-metallic catalytic systems, contribute to the catalysis of the asymmetric or stereospecific synthetic processes via specific inclusion of the molecules. We hope that systematization and analysis of the recent developments in the application of cyclodextrins in asymmetric and stereospecific synthesis presented in this review will further facilitate the development of this field
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