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ChemInform Abstract: Solvent-Assisted Addition of Tetraallylic, Tetraallenic and Tetrapropargylic Stannanes to Aldehydes and Acetals.

✍ Scribed by A. MCCLUSKEY; I. W. MUDERAWAN; MUNTARI MUNTARI; D. J. YOUNG


Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


Solvent-Assisted

Addition of Tetraallylic, Tetraallenic and Tetrapropargylic Stannanes to Aldehydes and Acetals.

-The addition reaction of tetraallylic stannanes to aldehydes under conditions A) yields homoallylic alcohols, whereas analogous reactions with tetraallenic and tetrapropargylic stannanes result in a mixture of products with considerable allylic rearrangement. Exclusive rearrangement is observed for methyl-substituted substrates (XI) and (XIV). The reaction of (IV) and (VII) with benzaldehyde dimethylacetal (X), catalyzed by TFA, provides (VIa) and (VIIIa) highly regioselectively with allylic rearrangement. -(MCCLUSKEY, A.; MUDERAWAN,


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