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

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

doi:10.1055/s-1998-1807

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 journal › Article › peer-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 language	English
Pages (from-to)	909-911
Number of pages	3
Journal	Synlett
Volume	1998
Issue number	8
DOIs	https://doi.org/10.1055/s-1998-1807
Publication status	Published - 1998
Externally published	Yes

Access to Document

10.1055/s-1998-1807

Link to publication in Scopus

Cite this

@article{572219b10a6e495b9397107b1c7c5bc8,

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

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.",

author = "Adam McCluskey and Muderawari, {I. Wayan} and Muntari and Young, {David J.}",

year = "1998",

doi = "10.1055/s-1998-1807",

language = "English",

volume = "1998",

pages = "909--911",

journal = "Synlett: accounts and rapid communications in synthetic organic chemistry",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "8",

}

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

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0042248624&partnerID=8YFLogxK

U2 - 10.1055/s-1998-1807

DO - 10.1055/s-1998-1807

M3 - Article

AN - SCOPUS:0042248624

VL - 1998

SP - 909

EP - 911

JO - Synlett: accounts and rapid communications in synthetic organic chemistry

JF - Synlett: accounts and rapid communications in synthetic organic chemistry

SN - 0936-5214

IS - 8

ER -

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

Abstract

Access to Document

Fingerprint

Cite this