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Relative and Absolute Structure Assignments of Alkenes Using Crystalline Osmate Derivatives for X-ray Analysis

Authors :
Paul R. Carlson
Charles J. Dooley
Joseph W. Ziller
Scott D. Rychnovsky
Alexander S. Burns
Source :
Organic Letters. 21:10125-10129
Publication Year :
2019
Publisher :
American Chemical Society (ACS), 2019.

Abstract

Osmium tetroxide and TMEDA form stable crystalline adducts with alkenes. The structure of liquid alkenes can be determined through X-ray analysis of these derivatives. Osmium, a heavy atom, facilitates the crystallographic analysis and the determination of the absolute configuration using common Mo X-ray sources. The utility of this method for assigning structures and absolute configurations was demonstrated on a number of unsaturated substrates that include simple alkenes, enones, enol ethers, and silyl enol ethers.

Details

ISSN :
15237052 and 15237060
Volume :
21
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....a5b6c271b8b3a77fdbdcf7392beff678