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

Adam McCluskey, I. Wayan Muderawari, Muntari, David J. Young

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)909-911
Number of pages3
JournalSynlett
Volume1998
Issue number8
DOIs
Publication statusPublished - 1998
Externally publishedYes

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Acetals
Tin
Aldehydes
Methanol
Alcohols
stannane

Cite this

McCluskey, Adam ; Muderawari, I. Wayan ; Muntari, ; Young, David J. / Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals. In: Synlett. 1998 ; Vol. 1998, No. 8. pp. 909-911.
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abstract = "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.",
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Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals. / McCluskey, Adam; Muderawari, I. Wayan; Muntari, ; Young, David J.

In: Synlett, Vol. 1998, No. 8, 1998, p. 909-911.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals

AU - McCluskey, Adam

AU - Muderawari, I. Wayan

AU - Muntari,

AU - Young, David J.

PY - 1998

Y1 - 1998

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AB - 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.

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U2 - 10.1055/s-1998-1807

DO - 10.1055/s-1998-1807

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