4,4-Dimethyl-3,5,8-trioxabic-yclo[5,1,0]Octane

Chemical Properties

Clear colorless to yellow liquid

Uses

4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane is used in the CO2-mediated formation of chiral carbamates from meso-epoxides via polycarbonate intermediates and amine nucleophiles, which opens up a wide a wide range of CO2-based carbamate scaffolds with excellent yields and 99% enantiomeric excess.

Application

4, 4-dimethyl-3,5, 8-trioxane [5,1,0] octane is a key intermediate in the preparation of gadobinol. As a meso epoxide, it could be used to obtain optically pure ABT derivatives through Ti(IV)/BINOL catalyzed asymmetric aminolysis[1].

References

[1] Bao H, et al. Insight into the Mechanism of the Asymmetric Ring-Opening Aminolysis of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane Catalyzed by Titanium/BINOLate/Water System: Evidence for the Ti(BINOLate)2-Bearing Active Catalyst Entities and the Role of Water. Journal of the American Chemical Society, 2008; 130: 10116–10127.