Cover Feature: Stereoselectivity Enhancement During the Generation of Three Contiguous Stereocenters in Tetrahydrothiophenes (2/2021)

Abstract

The Cover Feature shows that Cinchona hits the bull's‐eye! In their Full Paper, Ż. A. Mała et al. describe step‐by‐step how chiral Cinchona alkaloid squaramide plays a key role in the decomposition of dithiane diol to generate reactive mercaptoaldehyde. This reactive species adds to various en‐ynones in stereoselective fashion under the control of a bifunctional hydrogen‐bonding system. The Kohn‐Sham Density Functional Theory calculations indicate the key role of the weak π‐stacking interactions in achieving the favorable orientation of the reagents. As a result, chiral tetrahydrothiophenes with a triple bond close to the sulfur atom and the three contiguous stereocenters are formed. More information can be found in the Full Paper by Ż. A. Mała et al.