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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.

Authors

A.P. Lightfoot

S.J.R. Twiddle



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