Palldium-Catalyzed Synthesis of Epoxides by Carboetherification

Significance

A new method for the synthesis of epoxides from tertiary allyl alcohols and aryl halides is reported. The methodology is based on Wolfe’s carboetherification reaction (J. S. Nakhla, J. W. Kampf, J. P. Wolfe J. Am. Chem. Soc. 2006, 128, 2893) and involves the tandem formation of C-C and C-O bonds. The broad scope includes stereoselective versions with dr values in excess of 99:1. For these reactions, the yields and diastereoselectivities increased as bulkier substituents were present on the tertiary alcohol.