Related Experiment Video
Updated: Jan 20, 2026

Negative Additive Manufacturing of Complex Shaped Boron Carbides
Published on: September 18, 2018
Wittig Rearrangements of Boron-Based Oxazolidinone Enolates
Zirong Zhang1, David B Collum1
1Department of Chemistry and Chemical Biology Baker Laboratory , Cornell University , Ithaca , New York 14853-1301 , United States.
Abstract:
[2,3]-Sigmatropic rearrangements (Wittig rearrangements) of α-alkoxy oxazolidinone enolates are described. Whereas alkali metal enolates fail, owing to facile deacylation, boron enolates generated from di-n-butylboron triflate and triethylamine rearranged in good yields and high selectivities with exceptions noted. IR and NMR spectroscopies show the boron is chelated by the α-alkoxy group rather than the more distal oxazolidinone carbonyl in the complex and enolate. The rearrangement product contains a boron alkoxide that remains unchelated by either carbonyl. Optimization was guided by density functional theory computations, suggesting that valine-derived oxazolidinones would be superior to the phenylalanine-derived analogues.
More Related Videos
13:09Assessment of Boron Doped Diamond Electrode Quality and Application to In Situ Modification of Local pH by Water Electrolysis
Published on: January 6, 2016
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Types of Enols and Enolates
Reactivity of Enols
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Lewis Acids and Bases
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Reactivity of Enolate Ions