Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals

A McCluskey; I W Muderawari; Muntari Young; David James Young

doi:10.1055/s-1998-1807

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Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals

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Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals

A McCluskey, I W Muderawari, Muntari Young and David James Young

Synlett, Vol.8, pp.909-911

1998

DOI: https://doi.org/10.1055/s-1998-1807

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Abstract

organostannanes

homoallylic alcohols

allenes

alkynes

Tetraallylic, tetraallenic and tetrapropargylic stannanes (0.25 eq) react with aldehydes 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 Sc and tetra(2-butynyl)tin 6e. The corresponding TFA catalysed reactions of dimethyl acetals with Sc and 6e are highly regioselective with allylic rearrangement.

Details

Title: Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals
Authors: A McCluskey (Author) - University of Newcastle
I W Muderawari (Author) - University of Newcastle
Muntari Young (Author) - University of Newcastle
David James Young (Author)
Publication details: Synlett, Vol.8, pp.909-911
Publisher: Georg Thieme Verlag
Date published: 1998
DOI: 10.1055/s-1998-1807
ISSN: 0936-5214
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449494502621
Output Type: Journal article

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