Asymmetric Synthesis of Fused Tetrahydroquinolines via Intra-molecular Aza-Diels-Alder Reaction of ortho -Quinone Methide Imines

被引：7

作者：

Hofmann, Fabian ^{[1
]}

Gaertner, Cornelius ^{[1
]}

Kretzschmar, Martin ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, Fak Chem & Mineral, Johannisallee 29, D-04103 Leipzig, Germany

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 04期

关键词：

aza-Diels-Alder reactions; ortho -quinone methide imines; Bronsted acid catalysis; N -triflyl phosphoric amide; tetrahydroquinolines; HIGHLY ENANTIOSELECTIVE SYNTHESIS; 4+2 CYCLOADDITION; ACID CATALYSIS; BETA-DICARBONYLS; SULFUR YLIDES; CONSTRUCTION; SUBSTITUTION; DERIVATIVES; 1-AZADIENES; ACTIVATION;

D O I：

10.1055/a-1517-7515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza-Diels-Alder reactions are straightforward processes for the construction of N -heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow the formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Bronsted acid bound ortho -quinone methide imines to generate a range of interesting fused tetrahydroquinolines in a diastereo- and enantioselective- manner.

引用

页码：1055 / 1080

页数：26

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