通过氧化生成的芳基阳离子进行的双分子偶联反应：范围和立体控制
Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.
作者信息
Cui Yubo, Villafane Louis A, Clausen Dane J, Floreancig Paul E
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, Telephone: (+1)412-62408727.
出版信息
Tetrahedron. 2013 Sep 9;69(36):7618-7626. doi: 10.1016/j.tet.2013.05.011.
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 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.
摘要
色烯、异色烯和苯并二氢噻唑与2,3-二氯-5,6-二氰基-1,4-苯醌反应形成稳定的芳香阳离子，这些阳离子可与一系列亲核试剂反应。这些氧化片段偶联反应能快速构建结构多样的杂环化合物。在手性布朗斯特酸存在下进行反应会形成不对称离子对，这在通过氧化碳氢键裂解生成手性亲电试剂而实现的立体选择性过程的罕见例子中，能够提供对映体富集的产物。
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