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 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
Andrew P
AP
GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK.
Twiddle
Steven J R
SJ
Whiting
Andrew
A
D000475:Alkenes / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
C506705:4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane; D000475:Alkenes; D001896:Boron Compounds; D004146:Dioxanes; D007462:Iodobenzenes; D008024:Ligands; C031905:iodobenzene