78284-53-4Relevant academic research and scientific papers
From the gold-catalysed benzylation of arenes to the regio- and stereoselective synthesis of procyanidins dimers
Fabre, Sandy,Gueroux, Marie,Nunes, Emeline,Szlosek-Pinaud, Magali,Pianet, Isabelle,Fouquet, Eric
, p. 3045 - 3051 (2015/05/04)
This work reports on a new intermolecular C-C coupling reaction between electron rich arenes and benzylic alcohols or ethers, catalysed by gold(III) salts, or other catalysts such as gold(I) and iron (III), and its application to the regio- and stereoselective synthesis of procyanidins dimers B1 and B3.
Synthesis of Condensed Tannins. Part 1. Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols, and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism
Botha, Jacobus J.,Young, Desmond A.,Ferreira, Daneel,Roux, David G.
, p. 1213 - 1219 (2007/10/02)
Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues.Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects.The sign of high intensity Cotton effects to low wavelength, contributed by aryl chromophores at C-4, may almost invariably be correlated with the absolute configuration at this chiral centre of 2,3-trans-3,4-trans, 2,3-trans-3,4-cis, and 2,3-cis-3,4-trans-isomers.
