Cu_Zn_Organometallics

Reaction of Organocuprates
Stereochemistry of 1,4-addition
• Note that the 4-methylcyclohexenone gives preferentially the
trans-product.
• In this case, the reaction proceeds via a conformation with the
Me group being pseudoaxial due to A 1,2 strain.
• addition of organocuprates to enones followed by alkylation of
resultant enolates generates 2 C-C bonds in a single reaction