The stereoselective synthesis of trisubstituted alkenes has become a key topic in modern organic chemistry. At the same time, trisubstituted alkenes also serve as valuable starting materials for a wide range of transformations. However, it remains unclear to what extent these alkenes are utilized in comparison to their mono- and disubstituted counterparts. This review aims to provide a comprehensive overview of fundamental transformations involving all-carbon-substituted trisubstituted alkenes. The first section focuses on additions of carbon, oxygen, and nitrogen nucleophiles, as well as halogenation and carboxylation reactions. The second part discusses oxidative cleavage processes, while the final section addresses the cyclization and cycloisomerization reactions of trisubstituted alkenes.
In 2019, carbamates derived from 3-hydroxypyridine were classified as nerve agents and subsequently included in the Annex on Chemicals by the Conference of the States Parties. Herein, we describe the preparation of a structural simulant of this class of compounds, 10-hydroxy-N,N-dimethyl-N-((3-(tosyloxy)pyridin-2-yl)methyl)decan-1-aminium bromide. The compound was synthesized via tosylation of 2-((N,N-dimethylamino)methyl)pyridin-3-ol with tosyl chloride in the presence of sodium hydride, followed by alkylation of the resulting ((N,N-dimethylamino)methyl)pyridin-3-yl 4-methylbenzenesulfonate with 10-bromodecan-1-ol.