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

被引：40

作者：

Cui, Yubo ^{[1
]}

Villafane, Louis A. ^{[1
]}

Clausen, Dane J. ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2013年 / 69卷 / 36期

关键词：

Oxidation; Fragment coupling; Heterocycles; Chiral counterions; Enantioselectivity; CHIRAL BRONSTED ACID; STEREOSELECTIVE-SYNTHESIS; CARBOCATION FORMATION; CATALYTIC AMOUNTS; CHROMENE ACETALS; DUAL CATALYSIS; ETHERS; DDQ; ACTIVATION; DEPROTECTION;

D O I：

10.1016/j.tet.2013.05.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Bronsted 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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7618 / 7626

页数：9

共 77 条

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