Tetrahedron

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

Y Cui, LA Villafane, DJ Clausen, PE Floreancig

Index: Cui, Yubo; Villafane, Louis A.; Clausen, Dane J.; Floreancig, Paul E. Tetrahedron, 2013 , vol. 69, # 36 p. 7618 - 7626

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Citation Number: 16

Abstract

Abstract 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 ...