| Title | Axial Chirality Control During Suzuki-Miyaura Cross-Coupling Reactions: The tert-Butylsulfinyl Group as an Efficient Chiral Auxiliary. | | Author(s) | Colobert F, Valdivia V, Choppin S, Leroux FR, Fernández I, Álvarez E, Khiar N | | Institution | Laboratoire de Stereochimie (UMR CNRS 7509), Universite de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 2, France, Instituto de Investigaciones Quimicas, C.S.I.C-Universidad de Sevilla, c/Americo Vespucio, 49, Isla de la Cartuja, 41092 Sevilla, Spain, and Departamento de Quimica Organica y Farmaceutica, Facultad de Farmacia, Universidad de Sevilla, c/Professor Gracia Gonzalez, 2, 41012 Sevilla, Spain. | | Source | Org Lett 2009 Oct 19. | | Abstract | 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. | | Language | ENG | | Pub Type(s) | JOURNAL ARTICLE
| | PubMed ID | 19839613 |
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