Conversion of epoxides to 1,3-dioxolanes catalyzed by tin(II) chloride.
Anhydrous tin(II) chloride is an efficient catalyst for the reaction of epoxides with acetone to prepare 2,2-dimethyl-1,3-dioxolanes (acetonides) in good to excellent yields. Mono-, di-, and trisubstituted epoxides participate equally well in this diastereospecific reaction. The use of single enantiomer epoxides under the reported conditions results in significant erosion of optical activity.
Vyvyan
James R
JR
Department of Chemistry, Western Washington University, Bellingham, WA 98225-9150, USA. vyvyan@chem.wwu.edu
Meyer
Jennifer A
JA
Meyer
Korin D
KD