607356-22-9Relevant academic research and scientific papers
An asymmetric biaryl Suzuki cross-coupling reaction: Stereogenic benzylic carbinols as chiral auxiliaries
Broutin, Pierre-Emmanuel,Colobert, Francoise
, p. 1113 - 1128 (2007/10/03)
Asymmetric biaryl Suzuki coupling reactions were performed with various aryl- or naphthylhalide-bearing enantiomerically pure benzylic alcohols and aryl- or naphthylboronic acids (or esters). The stereogenic benzylic alcohol was introduced by diastereoselective reduction of the arylhalide bearing a β-keto sulfoxide. In the presence of Pd(OAc)2/CsF and dppf or PPh3 excellent yields and atropodiastereoselectivities were obtained. The absolute configurations of the biaryls were determined by X-ray crystallography and 1H NMR NOESY experiments. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Efficient stereochemical controllers in biaryl Suzuki coupling reactions: Benzylic carbinols bearing in β-position thioether, dimethylamino, or sulfoxide groups
Broutin, Pierre-Emmanuel,Colobert, Francoise
, p. 3737 - 3740 (2007/10/03)
(Chemical Equation Presented) Highly atropo-diastereoselective Suzuki coupling between aryl halides bearing stereogenic benzylic carbinols with sulfoxide, thioether, or dimethylamino groups as efficient internal chelating ligands and 2-methoxy-1-naphthylboronic acid were performed with high yields; a palladacycle is proposed as a potential transition state.
Enantiopure β-hydroxysulfoxide derivatives as novel chiral auxiliaries in asymmetric biaryl suzuki reactions
Broutin, Pierre-Emmanuel,Colobert, Francoise
, p. 3281 - 3284 (2007/10/03)
Highly diastereoselective biaryl Suzuki coupling reactions of (1R)-1-(2-iodo or bromophenyl)-2-(R)-(4-tolylsulfinyl)-1-ethanol derivatives with various aryl- or naphthylboronic acids (or esters) were performed with high yields (up to 99%) and an excellent control of the axial chirality (up to 98% de).
