Stereoselectivity of Organometallic Reagents Addition to 7-Oxabicyclohept-5-en-2-one

Article abstract of DOI:10.1021/jo00278a032

The reaction between 7-oxabicyclo<2.2.1>hept-5-en-2-one and a variety of organolithium, Grignard, and organocuprate reagents is described.Organolithium and Grignard reagents yield the expected endo alcohols with high selectivity.Alternatively, lithium organocuprates add with high stereoselectivity to the hindered endo face of the carbonyl functionality to afford the corresponding exo alcohols.