C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

Benzene hydrogenation is an important industrial process. The reaction is incomplete, resulting in a mixture of benzene, cyclohexane, and/or cyclohexene that have to be separated before any further reactions. The currently used extractive and azeotropic distillations are operationally complex and energy intensive. Adsorptive separation provides an alternative energy-efficient method. However, the separation of the ternary mixture by adsorptive separation has not yet been reported. In the present research, we report two macrocyclic hosts with hydrogen-bonding sites in their cavities that are able to separate the ternary mixture of benzene, cyclohexene, and cyclohexane. NÀH•••p interactions were found to play a key role in the selective separation. In addition, fast adsorption, high loading ratios, and easy recycling are achieved with the present system, which is promising for practical applications.

Induced fit and conformational selection are two dominant binding mechanisms in biology. Although induced fit has been widely accepted by supramolecular chemists, conformational selection is rarely studied with synthetic systems. In the present research, we report a macrocyclic host whose binding mechanism is unambiguously assigned to conformational selection. The kinetic and thermodynamic aspects of this system are studied in great detail. It reveals that the kinetic equation commonly used for conformational selection is strictly followed here. In addition, two mathematical models are developed to determine the association constants of the same guest to the two host conformations. A “conformational selectivity factor” is defined to quantify the fidelity of conformational selection. Many details about the kinetic and thermodynamic aspects of conformational selection are revealed by this synthetic system. The conclusion and the mathematical models reported here should be helpful in understanding complex molecular recognition in both biological and synthetic systems.

Optical methods are promising to address the ever‐increasing demands for chirality analysis in drug discovery and related fields because they are amenable to high‐throughput screening. Circular dichroism‐based chiroptical sensing using host‐guest chemistry is especially appealing due to the fast equilibrium kinetics, wide substrate scope, and potential for sustainable development. In this Minireview, we give an overview on this emerging field. General aspects of molecular recognition and chirality transfer are analyzed. Chirality sensors are discussed by dividing them into three classes according to their structural features. Applications of these chirality sensors for chirality analysis of the products of asymmetric reactions and for the real‐time monitoring of reaction kinetics are demonstrated with selected examples. Moreover, challenges and research directions in this field are also highlighted.

Optical chirality sensing has attracted a lot of interest due to its potential in high‐throughput screening in chirality analysis. A molecular sensor is required to convert the chirality of analytes into optical signals. Although many molecular sensors have been reported, sensors with wide substrate scope remain to be developed. Herein, we report that the amide naphthotube‐based chirality sensors have an unprecedented wide scope for chiroptical sensing of organic molecules. The substrates include, but are not limited to common organic products in asymmetric catalysis, chiral molecules with inert groups or remote functional groups from their chiral centers, natural products and their derivatives, and chiral drugs. The effective chirality sensing is based on biomimetic recognition in water and on effective chirality transfer through guest‐induced formation of a chiral conformation of the sensors. Furthermore, the sensors can be used in real‐time monitoring on reaction kinetics in water and in determining absolute configurations and ee values of the products in asymmetric catalysis.