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.
Professor Andrew Whiting firstname.lastname@example.org
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.
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|
|Publisher||Royal Society of Chemistry|
|Peer Reviewed||Peer Reviewed|