Journal
TETRAHEDRON
Volume 72, Issue 34, Pages 5208-5220Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.01.047
Keywords
Biaryl; Aryne C-C coupling; Atropo-diastereoselective; Organolithium; Sulfoxide; Oxazoline; Diether
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Funding
- CNRS (Centre National de la Recherche Scientifique, France)
- Malian government
- Ministere de l'Education Nationale et de la Recherche' (France)
- French 'Agence Nationale pour la Recherche' [ANR-14-CE06-0003-01]
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The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection. (C) 2016 Elsevier Ltd. All rights reserved.
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