Tetrahedron p. 545 - 556 (1989)
Update date:2022-08-04
Topics:
Corey, E. J.
Hannon, Francis J.
Boaz, Neil W.
A test has been made of a stereochemical prediction for conjugate addition based on the intermediacy of d,?*-complexes in the reaction of organocopper reagents with α,β-enones.The chiral α,β-enone 7 has been synthesized and subjected to reaction with various methyl cuprate reagents.Under conditions favorable to lithium chelation to the α-alkoxycarbonyl system of 7, conjugate addition to 7 was found to proceed with high (13:1 to 33:1) 1,4-diastereoselectivity, the configuration of the major diastereomer being that predicted by the d,?*-complex model.A new and especially diastereoselective reagent has been generated by the reaction of LiCuMe2 with 0.3 equivalent of water, a possible structure for which is presented.
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