A stereoselective synthesis of 1,6-diphenyl-1,3,5-hexatrienes utilising 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane as a two-carbon alkenyl building block

A number of 1,6-diphenyl-1,3,5-hexatrienes of varying alkene geometries were stereoselectively prepared from just two starting materials: iodobenzene and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane via a series of Heck, Suzuki-Miyaura and stereocontrolled iododeboronation reactions. These results de...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-09, Vol.3 (17), p.3167-3172
Main Authors: Lightfoot, Andrew P, Twiddle, Steven J R, Whiting, Andrew
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Boron Compounds - chemistry
Dioxanes - chemistry
Iodobenzenes - chemistry
Ligands
Molecular Structure
Stereoisomerism
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Summary:A number of 1,6-diphenyl-1,3,5-hexatrienes of varying alkene geometries were stereoselectively prepared from just two starting materials: iodobenzene and 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane via a series of Heck, Suzuki-Miyaura and stereocontrolled iododeboronation reactions. These results demonstrate how 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane can be used as a genuine two-carbon vinyl-dianion building block in stereocontrolled polyene synthesis.
ISSN:1477-0520
1477-0539
DOI:10.1039/b507900d