Chalcogen Chemistry: Fundamentals and Applications
Chapter 10: Chiral Selenium and Tellurium-containing Derivatives: Synthesis and Applications
Published:15 Feb 2023
Agata. J. Pacuła-Miszewska, Jacek Ścianowski, Dorota Krasowska, Jozef Drabowicz, 2023. "Chiral Selenium and Tellurium-containing Derivatives: Synthesis and Applications", Chalcogen Chemistry: Fundamentals and Applications, Vito Lippolis, Claudio Santi, Eder J. Lenardão, Antonio L. Braga
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The presence of heteroatoms in organic molecules is the key feature that makes them reactive and susceptible to transformation. The chemistry of heterorganic compounds is a very broad field of research covering almost all developing branches of organic chemistry among which the group of organochalcogens plays an important role. Their applicability in organic synthesis as reagents and catalyst, in material science, and as bio-active compounds has been studied for decades and is still evolving. Herein, the synthesis and applicability of chiral organoselenium and organotellurium compounds will be presented, focusing on the most recent reports with a brief historical background.
In 1973, when Sharpless reported that diphenyl diselenide could efficiently convert epoxides to allylic alcohols through selenoxide elimination,1 a new scientific field emerged – the development of reagents possessing a highly reactive selenium center. Rapid evolution of research expertise revealed that organoselenium compounds could be easily used as electrophilic, nucleophilic, and radical reagents to selectively functionalize more complex molecules. Facile manipulation of the incorporated Se-moiety, including its elimination from the final product's structure, along with mild reaction conditions, increased the popularity of Se-mediated protocols, e.g., selenenylations, selenocyclizations, SeO2-eliminations, and 2,3-sigmatropic rearrangements. Many current chapters and reviews summarize these Se-mediated transformations.2