Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne

Simon Simpkins; Benson Kariuki; Caterina Arico; Liam Cox

doi:10.1021/ol035536e

Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne

Simon Simpkins
, Benson Kariuki
, Caterina Arico
, Liam Cox

Chemistry

Research output: Contribution to journal › Article

25 Citations (Scopus)

Abstract

[reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.

Original language	English
Pages (from-to)	3971-3974
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	21
DOIs	https://doi.org/10.1021/ol035536e
Publication status	Published - 16 Oct 2003

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10.1021/ol035536e

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title = "Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne",

abstract = "[reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.",

author = "Simon Simpkins and Benson Kariuki and Caterina Arico and Liam Cox",

year = "2003",

month = oct,

day = "16",

doi = "10.1021/ol035536e",

language = "English",

volume = "5",

pages = "3971--3974",

journal = "Organic Letters",

publisher = "American Chemical Society",

number = "21",

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Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne. / Simpkins, Simon; Kariuki, Benson; Arico, Caterina et al.
In: Organic Letters, Vol. 5, No. 21, 16.10.2003, p. 3971-3974.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne

AU - Simpkins, Simon

AU - Kariuki, Benson

AU - Arico, Caterina

AU - Cox, Liam

PY - 2003/10/16

Y1 - 2003/10/16

N2 - [reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.

AB - [reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.

UR - https://www.scopus.com/pages/publications/0242459917

U2 - 10.1021/ol035536e

DO - 10.1021/ol035536e

M3 - Article

C2 - 14535756

VL - 5

SP - 3971

EP - 3974

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Stereoselective synthesis of β-(chloro)vinylsilanes using a regio- and (E)-stereoselective Bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne

Abstract

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