Asymmetric Synthesis with Organoselenium Compounds – The Past Twelve Years

• Published in: Chemistry : a European journal 2024-04, Vol.30 (21), p.e202304074-n/a
• Main Authors: Stadel, Jessica T., Back, Thomas G.
• Format: Article
• Language: English
• Subjects: asymmetric catalysis; Asymmetric synthesis; Asymmetry; Catalysts; Chemical synthesis; chirality; Enantiomers; Literature reviews; Organoselenium compounds; Reagents; Selenium; Selenium compounds; stereochemistry; Substrates; synthetic methods
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202304074

The discovery and synthetic applications of novel organoselenium compounds and their reactions proceeded rapidly during the past fifty years and such processes are now carried out routinely in many laboratories. At the same time, the growing demand for new enantioselective processes provided new challenges. The convergence of selenium chemistry and asymmetric synthesis led to key developments in the 1970s, although the majority of early work was based on stoichiometric processes. More recently, greater emphasis has been placed on greener catalytic variations, along with the discovery of novel reactions and a deeper understanding of their mechanisms. The present review covers the literature in this field from 2010 to early 2023 and encompasses asymmetric reactions mediated by chiral selenium‐based reagents, auxiliaries, and especially, catalysts. Protocols based on achiral selenium compounds in conjunction with other species of chiral catalysts, as well as reactions that are controlled by chiral substrates, are also included. Examples of asymmetric reactions modulated by selenium compounds include a chiral selenophosphoramide Lewis base that catalyzes electrophilic and oxidative additions to alkenes, an ylide containing a terpene‐based chiral auxiliary for cyclopropanations and a chiral selenide catalyst for photoredox cyclofunctionalizations.