Details

Autor(en) / Beteiligte

• Cui, Yubo
• Villafane, Louis A.
• Clausen, Dane J.
• Floreancig, Paul E.

Titel

Bimolecular coupling reactions through oxidatively generated aromatic cations: scope and stereocontrol

Ist Teil von

• Tetrahedron, 2013-09, Vol.69 (36), p.7618-7626

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

2013

Link zum Volltext

Quelle

Elsevier ScienceDirect Journals Complete

Beschreibungen/Notizen

• Chromenes, isochromenes, and benzoxathioles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form stable aromatic cations that react with a range of nucleophiles. These oxidative fragment coupling reactions provide rapid access to structurally diverse heterocycles. Conducting the reactions in the presence of a chiral Brønsted acid results in the formation of an asymmetric ion pair that can provide enantiomerically enriched products in a rare example of a stereoselective process resulting from the generation of a chiral electrophile through oxidative carbon–hydrogen bond cleavage. [Display omitted]