1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies

被引：44

作者：

Albrecht, Lukasz ^{[1
]}

Gomez, Clarisa Villegas ^{[1
]}

Jacobsen, Christian Borch ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

DIELS-ALDER REACTION; ALPHA-ARYLATION; ACTIVATION; CATALYSIS; FUNCTIONALIZATION; 2,4-DIENALS; OXINDOLES; QUINONES; ACCESS; AMINE;

D O I：

10.1021/ol401204a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of optically active, carboannulated dihydronaphthoquinone and naphthoquinone derivatives with up to four stereogenic centers is demonstrated by H-bond-directed, trienamine-mediated [4 + 2]-cycloadditions. The outcome of the reaction between 2,4-dienals and 1,4-naphthoquinones is controlled by the substituent in the 2-position of the 1,4-naphthoquinone. In the case of sterically demanding 2-substituted derivatives, dihydronaphthoquinones are obtained. However, when a hydrogen atom is present in the 2-position, a subsequent oxidation of the initially formed cycloadducts occurs yielding naphthoquinones.

引用

页码：3010 / 3013

页数：4

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