期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 5, 页码 1735-1743出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503650
关键词
asymmetric synthesis; chirality; C-H activation; fluorine; olefination
资金
- CNRS (Centre National de la Recherche Scientifique)
- Ministere de l'Education Nationale et de la Recherche
- ANR (Agence Nationale de la Recherche), France
- Ministere de l'Education Nationale et de la Recherche, France
- CiRFC of Strasbourg
Axially chiral biaryls are ubiquitous structural motifs of biologically active molecules and privileged ligands for asymmetric catalysis. Their properties are due to their configurationally stable axis, and therefore, the control of their absolute configuration is essential. Efficient access to atropo-enantioenriched biaryl moieties through asymmetric direct C H activation, by using enantiopure sulfoxide as both the directing group (DG) and chiral auxiliary, is reported. The stereoselective oxidative Heck reactions are performed in high yields and with excellent atropo-stereoselectivities. The pivotal role of 1,1,1,3,3,3-hexafluoropropanol (HFIP) solvent, which enables a drastic increase in yield and stereoselectivity of this transformation, is evidenced and investigated. Finally, the synthetic usefulness of the herein disclosed transformation is showcased because the traceless character of the sulfoxide DG allows straightforward conversions of the newly accessed, atropopure sulfoxide-biaryls into several differently substituted axially chiral scaffolds.
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