A.P. Lightfoot
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
Lightfoot, A.P.; Twiddle, S.J.R.; Whiting, A.
Abstract
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.
Citation
Lightfoot, A., Twiddle, S., & Whiting, A. (2005). 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. Organic and Biomolecular Chemistry, 3(17), 3167-3172. https://doi.org/10.1039/b507900d
Journal Article Type | Article |
---|---|
Publication Date | Jul 1, 2005 |
Deposit Date | May 3, 2007 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 3 |
Issue | 17 |
Pages | 3167-3172 |
DOI | https://doi.org/10.1039/b507900d |
Public URL | https://durham-repository.worktribe.com/output/1569715 |
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