Diastereoselective ultrasonically induced zinc-copper conjugate addition to chiral α,β-unsaturated carbonyl systems in aqueous media.

Suárez, R. M.; Pérez Sestelo, J.; Sarandeses, L. A.


Synlett 2002, 1435–1438 (DOI: 10.1055/s-2002-33604).

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The diastereoselective ultrasonically induced zinc–copper 1,4-addition of alkyl iodides to chiral α,β-unsaturated systems in aqueous media is reported. The reaction of a methylenedioxolanone with a variety of alkyl iodides takes place in good yields and with high diastereomeric excess. The 1,4-addition to (Z)-and (E)-γ,δ-dioxolanyl-a,b-unsaturated esters also proceeds with good yields: the Z-isomer gives good diastereoselectivities while the reactions with the E-isomer are non-stereoselective.