Year: 2025
Type: article
Abstract: We previously demonstrated that osmium tetroxide and TMEDA generate stable crystalline adducts with alkenes that facilitate X-ray analysis and structure assignments. Alternatively, osmate esters can be prepared from diols, potassium osmate, and TMEDA·2TsOH in a nonoxidative condensation reaction. This new approach provides a convenient route to form stable, crystalline osmate(VI) esters for X-ray analysis. Because it is redox neutral, it works with a variety of diol substrates, including 1,3-diols, that cannot be prepared from alkenes. α-Hydroxy acids also form stable osmate esters in reasonable yields and readily crystallize. An alternative ligand screen was performed to assess the improved crystallinity from substituted TMEDA analogues. The enhanced crystallinity of osmate esters and the incorporation of a heavy atom make a reliable determination of structure and absolute configuration routine.
Source: The Journal of Organic Chemistry
Authors: Jordan C. Thompson, Ngoc H. Le, Jace Pluemer, Ruby Chen, Charles J. Dooley, Joseph W. Ziller, Scott D. Rychnovsky
Institution: University of California, Irvine
Language: English
Subfield: Spectroscopy
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4407163133