Application of Hydroxy Propargylic Alcohols in Organic Synthesis

Propargylic alcohol is a shining star in the chemical space. These congeners have garnered significant attention from the synthetic chemistry community due to their dual functionality and three-centered reactivity. In this realm, the electrophilic cyclization of propargylic alcohols with a tethered nucleophile functional group is a key strategy for synthesizing hetero- and carbocycles. In these transformations, the position of the nucleophilic reactive handle can influence the reaction outcome. Consequently, these derivatives open up numerous opportunities to create complex cyclic adducts through various reaction pathways. Among all nucleophile tethers, the hydroxy group has been increasingly used in the production of oxy-heterocyclics. The hydroxy dialing on the core propargylic alcohol would lead to oxy-heterocyclics, such as benzofuran, furan, chromene, coumarin, chromone, pyrane, etc., which have numerous applications in various fields of biology and other scientific fields. In this review, we focused on uncovered hydroxy-tethered propargylic alcohol cyclization reactions. We categorized these transformations based on the structural features of hydroxy propargylic alcohols. With this review, we aim to pave the way for further efforts in discovering new reaction pathways.