114744-47-7

Upstream product

• 95530-78-2 7-oxabicyclo[2.2.1]hept-5-en-2-one 
• 591-51-5 phenyllithium 

Downstream Products

• 133147-38-3 (1S*,3R*,6R*)-6-n-butyl-3-phenyl-cyclohex-4-en-1,3-diol 
• 133147-38-3 (1S*,3S*,6R*)-6-n-butyl-3-phenyl-cyclohex-4-en-1,3-diol 
• 133147-41-8 (1S*,3S*,6R*)-6-t-butyl-3-phenyl-cyclohex-4-en-1,3-diol 

Relevant academic research and scientific papers

STEREOSELECTIVITY OF THE REACTION BETWEEN 7-OXABICYCLOHEPT-5-EN-2-ONE AND ORGANOCUPRATE REAGENTS

Lithium organocuprates add with high stereoselectivity to the hindered endo face of the carbonyl group of 7-oxabicyclohept-5-en-2-one to yield the corresponding exo alcohols.

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

The reaction between 7-oxabicyclohept-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.