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.

Despite the fact that halogenation of alkenes has been known for centuries, enantioselective variants of this reaction have only recently been developed. In the past three years, catalytic enantioselective versions of halofunctionalizations with the four common halogens have appeared and although important breakthroughs, they represent just the very beginnings of a nascent field. This Minireview provides a critical analysis of the challenges that accompany the development of general and highly enantioselective halofunctionalization reactions. Moreover, the focus herein, diverges from previous reviews of the field by identifying the various modes of catalysis and the different strategies implemented for asymmetric induction.

Catalytic, Asymmetric Halofunctionalization of Alkenes—A Critical Perspective

During the past four years, the research of new synthetic methodologies for the rapid construction of enantiomerically pure substituted indole has had a fruitful and important growth This research line continues to produce stunning arrays of enantioselective technologies either metal or organocatalyzed Thus, an update of our previous review (Chem Soc Rev, 2010, 39, 4449–4465) has become necessary and this critical review documents the literature on this topic, until the end of 2013

Strategies for the asymmetric functionalization of indoles: an update.

Carbon dioxide (CO2) has emerged as a sustainable, feasible, abundant one-carbon synthon and displays great potential in the synthesis of heterocycles such as lactones, lactams, and 2-oxazolidinones, which are privileged motifs in pharmaceutical chemistry demonstrating bioactivities. Although the fixation of CO2 is restricted due to its thermodynamic stability and kinetic inertness, multiple breakthroughs have been realized in annulation chemistry. This review concentrates on the advances made in the last five years in CO2-incorporated cyclization triggered by N-, O-, and C-nucleophiles. Three transformation modes of CO2 including carboxylative cyclization, carbonylative cyclization, and reductive cyclization have been summarized. Moreover, typical mechanisms and significant applications of these reactions are also described.

Recent advances in nucleophile-triggered CO2-incorporated cyclization leading to heterocycles.

Synthetic approaches to 3-(2-nitroalkyl) indoles and their use to access tryptamines and related bioactive compounds.

Highly enantioselective halolactonizations have been developed using a chiral proton catalyst NIS reagent system in which the Bronsted acid is used at catalyst loadings as low as 1 mol%. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand proton complex present at low catalyst loadings) to optimize enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yield (up to 98% ee) using commercially available N-iodosuccinimide (NIS).

Achiral Counterion Control of Enantioselectivity in a Brønsted Acid-Catalyzed Iodolactonization

Carbon dioxide exhibits many of the qualities of an ideal reagent: it is nontoxic, plentiful, and inexpensive. Unlike other gaseous reagents, however, it has found limited use in enantioselective synthesis. Moreover, unprecedented is a tool that merges one of the simplest biological approaches to catalysis—Bronsted acid/base activation—with this abundant reagent. We describe a metal-free small molecule catalyst that achieves the three component reaction between a homoallylic alcohol, carbon dioxide, and an electrophilic source of iodine. Cyclic carbonates are formed enantioselectively.

/pdf/enantioselective-small-molecule-synthesis-by-carbon-dioxide-1q72w451r7.pdf

Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease

/pdf/preparation-of-h-4-pyrrolidinequin-bam-pbam-2gg61ekfxl.pdf

Preparation of H,4 PyrrolidineQuin‐BAM (PBAM)

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