Intramolecular epoxide openings

From :
Douglass F. Taber,* Lee J. Silverberg, and Edward D. Robinson
J. Am. Chem. SOC. 1991,113,6639-6645


1. nitrile anion opening and sulfone anions.

2.Nucleophilic allylic silanes have been employed, under acid-catalyzed conditions, ln
intramolecular epoxide openings.

3. Finally, StorkM has shown that ketone and ester enolates can be used to open allylic epoxides,
to form cyclohexane derivatives.

4. The only other enolate-based opening of an epoxide has been that reported by Negishi.31

(31)Z hang, Y.;M iller, J. A.; Negishi, E.-I.J . Org. Chem. 1989,54,2 043.