Gold-catalyzed synthesis of bicyclo[4.3.0]nonadiene derivatives via tandem 6-endo-dig/nazarov cyclization of 1,6-allenynes

被引：80

作者：

Lin, Guan-You ^{[1
]}

Yang, Chun-Yao ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 18期

关键词：

D O I：

10.1021/jo0707939

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic cyclization of 1,6-allenynes was achieved by AuPPh3SbF6 (5 mol %) in cold CH2Cl2 (0 degrees C, 0.5-4 h) to form bicyclo[4.3.0]nonadiene products; this cyclization proceeded more efficiently for a substrate bearing R = alkyl (yields > 70%). We propose a reaction mechanism involving a 6-endo-dig cyclization of Au(I)-pi-alkyne, followed by Nazarov cyclization.

引用

页码：6753 / 6757

页数：5

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