Stereoselective synthesis of beta-(Chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne

Simpkins, Simon M. E., Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Arico, Caterina S. and Cox, Liam R. 2003. Stereoselective synthesis of beta-(Chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: Application to the synthesis of a masked triyne. Organic Letters 5 (21) , pp. 3971-3974. 10.1021/ol035536e

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
ISSN:	1523-7060
Last Modified:	24 Oct 2022 11:11
URI:	https://orca.cardiff.ac.uk/id/eprint/47204

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