Synthesis of cis-3-Acyl-4-alkenylpyrrolidines via Gold(I)-Catalyzed Cycloisomerization Reaction of (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols

被引：14
|
作者：
Yeh, Ming-Chang P. [1 ]
Lin, Ming-Nan [1 ]
Chang, Wei-Jong [1 ]
Liou, Jia-Lun [1 ]
Shih, Ya-Fon [1 ]
机构：
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 17期
关键词：
GOLD CATALYSIS; 3,4-DISUBSTITUTED PYRROLIDINES; INTRAMOLECULAR HYDROAMINATION; ALPHA-AMINOALLENES; CYCLIZATION; ENYNES; ACIDS; 3-PYRROLINES; HETEROCYCLES; 1,6-ENYNES;
D O I：
10.1021/jo101148e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols were cycloisomerized to the corresponding cis-3-acyl-4-alkenylpyrrolidines when treated with a catalytic amount of Ph3PAuCl/AgOTf in CH(2)Cl(2). The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate cis-3-acyl-4-alkenylpyrrolidines in good yields. This transformation can be applied to the synthesis of cisand trans-3-acyl-4-alkenylcyclopentanes from (Z)- and (E)-8-aryloct-2-en-7-yn-1-ols, respectively.
引用
收藏
页码：6031 / 6034
页数：4
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