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  • Title: Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation: stereoselective synthesis of both erythro- and threo-homoallylic alcohols.
    Author: Hayashi S, Hirano K, Yorimitsu H, Oshima K.
    Journal: Org Lett; 2005 Aug 04; 7(16):3577-9. PubMed ID: 16048346.
    Abstract:
    Retro-allylation of bulky gallium homoallylic alkoxides occurs to generate (Z)- and (E)-crotylgallium reagents stereospecifically, starting from erythro- and threo-homoallylic alcohols, respectively. The (Z)- and (E)-crotylgallium reagents immediately reacted with aromatic aldehydes to afford the corresponding erythro- and threo-homoallylic alcohols, respectively. [reaction: see text]
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