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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

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

Andrew P Lightfoot, Steven J R Twiddle, Andrew Whiting

Org Biomol Chem. 2005 Sep 7;3(17):3167-72.

PMID: 16106297

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13826250	2,2′-Bi-1,3,2-dioxaborinane		13826-25-0	Price

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