An Asymmetric Organocatalytic Quadruple Cascade Initiated by a Friedel-Crafts-Type Reaction with Electron-Rich Arenes

被引：31

作者：

Erdmann, Nico ^{[1
]}

Philipps, Arne R. ^{[1
]}

Atodiresei, Iuliana ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 05期

关键词：

aniline derivatives; asymmetric synthesis; domino reactions; organocatalysis; quadruple cascade; CHIRAL BRONSTED ACID; TRICYCLIC CARBON FRAMEWORKS; DIELS-ALDER REACTION; DOMINO REACTIONS; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; PHOSPHORIC-ACID; ALPHA-ARYLATION; ALKYLATION;

D O I：

10.1002/adsc.201201099

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An organocatalytic quadruple domino reaction initiated by a FriedelCrafts-type reaction of electron-rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbaldehydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This diphenylprolinol trimethylsilyl ether-catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo- and excellent enantioselectivity.

引用

页码：847 / 852

页数：6

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