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Synlett 1998; 1998(8): 909-911
DOI: 10.1055/s-1998-1807
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Solvent Assisted Addition of Tetraallylic, Tetraallenic and Tetrapropargylic Stannanes to Aldehydes and Acetals

Adam McCluskey* , I Wayan Muderawan, Muntari Young, David J. Young
  • *Department of Chemistry, The University of Newcastle, University Drive, Callaghan, Newcastle, NSW Australia 2308; E-mail: amcclusk@mail.newcastle.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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Tetraallylic, tetraallenic and tetrapropargylic stannanes (0.25 eq) react with aldehydes in methanol to provide unsaturated alcohols. These reactions proceed in methanol to provide unsaturated alcohols. These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 5e and predominantly with allylic rearrangement for tetrapropadienyltin 5c and tetra(2-butynyl)tin 6e. The corresponding TFA catalysed reactions of dimethyl acetals with 5c and 6e are highly regioselective with allylic rearrangement.

organostannanes - homoallylic alcohols - allenes - alkynes