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  • Title: Diastereoselective additions of chiral vinylzinc reagents to alpha-chiral aldehydes.
    Author: Marshall JA, Eidam P.
    Journal: Org Lett; 2004 Feb 05; 6(3):445-8. PubMed ID: 14748614.
    Abstract:
    [reaction: see text] Additions of vinylic zinc bromide reagents to alpha-chiral aldehydes (R(1) = CH(2)OTBS, R(2) = Me; R(1) = Me, R(2) = OTBS) in the presence of lithiated (+)- or (-)-N-methylephedrine proceed with predominant reagent control to afford anti or syn adducts stereoselectively, except when the aldehydes possess an alkoxy substituent at the alpha- or beta-positions (R(1) = Me, R(2) = OBn; R(1) = CH(2)OBn, R(2) = Me), in which case chelation-controlled adducts predominate.
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