Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization

被引：49

作者：

Maier, Alexander F. G. ^{[1
]}

Tussing, Sebastian ^{[1
]}

Zhu, Hui ^{[2
]}

Wicker, Garrit ^{[1
]}

Tzvetkova, Pavleta ^{[3
,4
]}

Floerke, Ulrich ^{[1
]}

Daniliuc, Constantin G. ^{[5
]}

Grimme, Stefan ^{[2
]}

Paradies, Jan ^{[1
]}

机构：

[1] Univ Paderborn, Dept Chem, Warburger Str 100, D-33098 Paderborn, Germany

[2] Univ Bonn, Mulliken Ctr Theoret Chem, Beringstr 4, D-53115 Bonn, Germany

[3] Karlsruhe Inst Technol, Inst Organ Chem, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany

[4] Karlsruhe Inst Technol, Inst Biol Interfaces 4, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany

[5] Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 61期

关键词：

amines; borane catalysis; electrocyclization; hydride abstraction; tetrahydroquinoline; FRUSTRATED LEWIS PAIRS; RING-CLOSURE REACTIONS; BASIS-SETS; HETEROCYCLIC SYNTHESIS; CHEMISTRY; DIHYDROGEN; ACCURATE; B(C6F5)(3); DESIGN; PHASE;

D O I：

10.1002/chem.201804777

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The borane-catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum-mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 99% yield with a diastereoselectivity of > 99% in favour for the 3a-5-cis isomer.

引用

页码：16287 / 16291

页数：5

共 4 条

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[4] Diastereoselective Synthesis of Dihydro-quinolin-4-ones by a Borane-Catalyzed Redox-Neutral endo-1,7-Hydride Shift
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