Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 17, Pages 4668-4672Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801130
Keywords
asymmetric C-H activation; atropisomerism; axial chirality; chiral ligands; sulfoxides
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Funding
- CNRS (Centre National de la Recherche Scientifique)
- Ministere de l'Education Nationale et de la Recherche
- Ministere de l'Education Nationale et de la Recherche, France
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Herein we disclose the synthesis of original chiral scaffoldsortho-orientated terphenyls presenting two atropisomeric Ar-Ar axes. These unusual structures were built up by using the C-H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo-stereoselective C-H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho-terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N-Biax and diphosphine BiaxPhos.
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