Remote Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acid Catalysts for the Enantioselective Diels-Alder Reaction

被引：16

作者：

Hatano, Manabu ^{[1
]}

Ishihara, Hideyuki ^{[1
]}

Goto, Yuta ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648603, Japan

来源：

SYNLETT | 2016年 / 27卷 / 04期

关键词：

Diels-Alder reaction; phosphoric acid; BrOnsted acid; Lewis acid; supramolecular catalyst; chiral cavity; molecular recognition; SUPRAMOLECULAR CATALYSIS; SALT;

D O I：

10.1055/s-0035-1560369

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：564 / 570

页数：7

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