Journal of Organic Chemistry p. 4158 - 4164 (1989)
Update date:2022-08-03
Topics:
Arjona, Odon
Pradilla, Roberto Fernandez de la
Mallo, Araceli
Perez, Sonia
Plumet, Joaquin
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.
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