Applications of Supramolecular Anion Recognition

Charged intermediates and reagents are ubiquitous in organic transformations. The interaction of these ionic species with chiral neutral, anionic, or cationic small molecules has emerged as a powerful strategy for catalytic, enantioselective synthesis. This review describes developments in the burgeoning field of asymmetric ion-pairing catalysis with an emphasis on the insights that have been gleaned into the structural and mechanistic features that contribute to high asymmetric induction.

/pdf/asymmetric-ion-pairing-catalysis-2sl1xs8pug.pdf

Asymmetric ion-pairing catalysis.

Spirooxindoles have become a privileged skeleton given their broad and promising activities in various therapeutic areas. The strategies and catalyst systems described here highlight recent advances in the enantioselective synthesis of spirooxindoles via organocascade strategies. Various organocatalysts with distinct activation modes have found application in constructing these sophisticated compounds. This review focuses on the enantioselective synthesis of spirooxindoles via organocascade strategies and is organized on the basis of three primary starting materials and then further subdivided according to the types of organocatalyst. These methods are of importance for the synthesis of complex natural products and the design of new pharmaceutical compounds. We believe that compounds based on spirooxindole skeletons have the potential to provide novel therapeutic agents and useful biological tools.

https://www.scripps.edu/barbas/pdf/ChengACSCatal2014.pdf

Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies

Novel concepts in asymmetric catalysis have the potential to open up previously inaccessible reaction space. This Review reflects on the origins of an area that has undergone dramatic recent advancement: the use of chiral anions in asymmetric catalysis. Details of a selection of the latest examples are also given.

/pdf/the-progression-of-chiral-anions-from-concepts-to-4wofp3ao4d.pdf

The progression of chiral anions from concepts to applications in asymmetric catalysis

Supramolecular catalysis is a rapidly expanding discipline which has benefited from the development of both homogeneous catalysis and supramolecular chemistry. The properties of classical metal and organic catalysts can now be carefully tailored by means of several suitable approaches and the choice of reversible interactions such as hydrogen bond, metal–ligand, electrostatic and hydrophobic interactions. The first part of these two subsequent reviews will be dedicated to catalytic systems for which non-covalent interactions between the partners of the reaction have been designed although mimicking enzyme properties has not been intended. Ligand, metal, organocatalyst, substrate, additive, and metal counterion are reaction partners that can be held together by non-covalent interactions. The resulting catalysts possess unique properties compared to analogues lacking the assembling properties. Depending on the nature of the reaction partners involved in the interactions, distinct applications have been accomplished, mainly (i) the building of bidentate ligand libraries (intra ligand–ligand), (ii) the building of di- or oligonuclear complexes (inter ligand–ligand), (iii) the alteration of the coordination spheres of a metal catalyst (ligand–ligand additive), and (iv) the control of the substrate reactivity (catalyst–substrate). More complex systems that involve the cooperative action of three reaction partners have also been disclosed. In this review, special attention will be given to supramolecular catalysts for which the observed catalytic activity and/or selectivity have been imputed to non-covalent interaction between the reaction partners. Additional features of these catalysts are the easy modulation of the catalytic performance by modifying one of their building blocks and the development of new catalytic pathways/reactions not achievable with classical covalent catalysts.

/pdf/supramolecular-catalysis-part-1-non-covalent-interactions-as-4sw3itqtq6.pdf

Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts.

Group 5 Metal Binaphtholate Complexes for Catalytic Asymmetric Hydroaminoalkylation and Hydroamination/Cyclization

A Dual-Catalysis/Anion-Binding Approach to the Kinetic Resolution of Allylic Amines

The approach utilizes the use of an achiral nucleophylic catalyst (PPY or DMAP) and a hydrogen-bonding chiral catalyst (CTU).

A Dual‐Catalysis/Anion‐Binding Approach to the Kinetic Resolution of Allylic Amines.

Highly enantioselective organocatalytic aldol additions of α-isothiocyanato imides to aldehydes are reported. These reactions provide convenient access to enantiomerically enriched and protected β-hydroxy-α-amino acids with catalyst loadings as low as 1 mol%.

Catalytic Enantioselective Aldol Additions of α-Isothiocyanato Imides to Aldehydes.

OF THE DISSERTATION ii PREFACE iv DEDICATION v ACKNOWLEDGEMENTS vi TABLE OF CONTENTS vii LIST OF TABLES xii LIST OF FIGURES xiii LIST OF SCHEMES xiv ABBREVIATIONS, SYMBOLS AND UNITS xxii

Development of hydrogen-bonding catalysts for the kinetic resolution of amines via anion-binding

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