Gold-Catalyzed Enantioselective Intramolecular Annulation of Ene-Yne-Carbonyls via Benzopyrylium-Type Intermediates

被引：9

作者：

Koshikawa, Takumi ^{[1
]}

Satoh, Masakazu ^{[1
]}

Masutomi, Koji ^{[1
]}

Shibata, Yu ^{[1
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 07期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

Annulation; Asymmetric catalysis; Ene-yne-carbonyls; Gold; Benzopyrylium-type Intermediates; 4+2 CYCLOADDITION; O-ALKYNYLBENZALDEHYDE; N-ALLENAMIDES; RHODIUM; BENZANNULATION; CYCLIZATION; 1,6-ENYNES; ENYNALS; O-ALKYNYL(OXO)BENZENES; 3-STYRYLINDOLES;

D O I：

10.1002/ejoc.201801537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been established that a cationic gold(I)/(R)-H-8-binap complex catalyzes the enantioselective intramolecular [4+2] annulation of benzene-linked ene-yne-carbonyls via benzopyrylium-type intermediates at room temperature to give chiral tricyclic compounds, bearing two stereogenic centers, as single diastereomers with moderate ee values. Interestingly, the reactions of sterically demanding naphthalene-linked ene-yne-carbonyls with the same gold(I) catalyst gave not only [4+2] annulation products but also [3+2] annulation products as minor products with good ee values.

引用

页码：1488 / 1492

页数：5

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