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Access to Atropisomerically Enriched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines
Author(s) -
Yalcouye Boubacar,
BerthelotBréhier Anaïs,
Augros David,
Panossian Armen,
Choppin Sabine,
Chessé Matthieu,
Colobert Françoise,
Leroux Frédéric R.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501503
Subject(s) - aryne , diastereomer , oxazoline , chemistry , stereoselectivity , axial symmetry , coupling reaction , reaction conditions , dendrimer , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , mathematics , geometry
We report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions were key to accessing the desired, highly substituted, atropisomerically enriched biarylic products. In one case, the two atropo‐diastereomers could be obtained in isomerically pure form by column chromatographic separation and their absolute configurations established by X‐ray crystallography. The stereoselectivity of the reaction seems to be governed by subtle parameters.