Remote Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acid Catalysts for the Enantioselective Diels-Alder Reaction
Remote Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acid Catalysts for the Enantioselective Diels-Alder Reaction
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DOI：
10.1055/s-0035-1560369
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发表时间：
2016-03-01
期刊：
影响因子：
2
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Hatano, Manabu;Ishihara, Hideyuki;Ishihara, Kazuaki
研制了三（五氟苯基）硼烷辅助手性超分子磷酸催化剂，用于-取代丙烯醛与环戊二烯的Diels-Alder模型反应。两个远配位的三（五氟苯基）硼烷应该有助于增加超分子催化剂活性中心的BrOnsted酸度，并为手性腔创造有效的体积。制备的超分子催化剂不仅可以作为共轭的BrOnsted酸-BrOnsted碱催化剂，还可以在中心添加非手性Lewis酸源（如儿茶酚硼烷）时作为双功能的Lewis酸-BrOnsted碱催化剂。
Tris(pentafluorophenyl)borane-assisted chiral supramolecular phosphoric acid catalysts were developed for the model Diels-Alder reaction of -substituted acroleins with cyclopentadiene. Two remotely coordinated tris(pentafluorophenyl)boranes should help to increase the BrOnsted acidity of the active center in the supramolecular catalyst and create effective bulkiness for the chiral cavity. The prepared supramolecular catalysts acted as not only conjugated BrOnsted acid-BrOnsted base catalysts but also bifunctional Lewis acid-BrOnsted base catalysts with the addition of a central achiral Lewis acid source such as catecholborane.