Axial chirality control during Suzuki-Miyaura cross-coupling reactions: the tert-butylsulfinyl group as an efficient chiral auxiliary.
An efficient route to a new family of axially chiral biaryl ligands by a Suzuki-Miyaura cross-coupling reaction between ortho,ortho'-disubstituted aryl iodides bearing in ortho position a tert-butyl or p-tolylsulfinyl group and ortho-substituted phenyl boronic acids or esters is described. The comparison between the t-BuSO and p-TolSO groups as chiral controllers is reported. The modularity of the approach is demonstrated by the preparation of a variety of enantiopure axially chiral mixed S/N and S/P ligands.
Laboratoire de Stéréochimie (UMR CNRS 7509), Université de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France. francoise.colobert@unistra.fr
Françoise
F
Colobert
Victoria
V
Valdivia
Sabine
S
Choppin
Frédéric R
FR
Leroux
Inmaculada
I
Fernández
Eleuterio
E
Alvarez
Noureddine
N
Khiar
D008968:Molecular Conformation; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D013457:Sulfur Compounds