Lewis acid-mediated intramolecular addition of silyl enol ethers to internal unactivated alkynes

被引：15

作者：

Imamura, K ^{[1
]}

Yoshikawa, E ^{[1
]}

Gevorgyan, V ^{[1
]}

Sudo, T ^{[1
]}

Asao, N ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 11期

关键词：

Lewis acid; silyl enol ethers; carbocyclization; alkynes;

D O I：

10.1139/cjc-79-11-1624

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, gave mono- and bicyclic beta,gamma -unsaturated ketones in good to excellent yields. On the other hand, the silyloxy-substituted cyclic vinylsilanes were obtained in moderate to high yields when the reactions were catalyzed by B(C6F5)(3) in the presence of triethylsilane. All the reactions proceeded via endo-fashion exclusively. The mechanisms of these regiospecific Lewis acid-assisted carbocyclizations are proposed.

引用

页码：1624 / 1631

页数：8

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