Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes

被引：34

作者：

Schweighauser, Luca ^{[1
]}

Bodoky, Ina ^{[2
]}

Kessler, Simon N. ^{[2
,5
]}

Haeussinger, Daniel ^{[2
]}

Donsbach, Carsten ^{[3
,4
]}

Wegner, Hermann A. ^{[1
]}

机构：

[1] Univ Giessen, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany

[2] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel, Switzerland

[3] Univ Marburg, Fachbereich Chem, Hans Meerwein Str, D-35043 Marburg, Germany

[4] Univ Marburg, WZMW, Hans Meerwein Str, D-35043 Marburg, Germany

[5] Stockholm Univ, Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 06期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; CHEMICAL SPACE; COMBINATORIAL CHEMISTRY; HETEROCYCLIC AZADIENES; CYCLOADDITION CASCADE; VINBLASTINE ANALOGS; O-QUINODIMETHANES; ORGANIC-SYNTHESIS; ENAMINES; BIOLOGY;

D O I：

10.1021/acs.orglett.6b00276

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino process consisting of an inverse and a normal electron-demand Diels-Alder reaction is presented for the formation of bridged tri- and tetracyclic 1,2,3,4-tetrahydronaphthalenes catalyzed by a bidentate Lewis acid. The products were synthesized in a one-pot reaction from commercially available starting materials and contain up to six stereogenic centers. The tetrahydronaphthalenes were isolated as single diastereomers and are derivatives of phenylethylamine, which is well-known as a scaffold of amphetamine or dopamine.

引用

页码：1330 / 1333

页数：4

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