Various olefins readily participate in the ene reaction with azodicarboxylates and in epoxidation/aziridination followed by ring opening �on water�. The presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) increases catalytic activity of water surface. The observed rate enhancement is unique to water and is negligible in methanol, ethyl acetate, and dichloromethane. Ene reaction can be readily conducted with recycled aqueous phase and �on bleach�. In situ epoxidation/aziridination followed ring opening by amines, 1,3-dicarbonyl compounds, and heterocycles furnish a variety of pharmaceutically relevant fragments. Limitations, selectivity, and a possibility for asymmetric transformations will be discussed.

Functionalization of alkenes �on water� without metals

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.