Stereocontrol in rare earth metal triflate-catalyzed 1,3-dipolar cycloaddition reaction of 2-benzopyrylium-4-olate with aldehydes

被引：32
|
作者：
Suga, H [1 ]
Kakehi, A
Ito, S
Inoue, K
Ishida, H
Ibata, T
机构：
[1] Shinshu Univ, Fac Engn, Dept Chem & Mat Engn, Wakasato, Nagano 3808553, Japan
[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 20期
关键词：
D O I：
10.1021/ol0063454
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Exo-cycloadduct was obtained with high stereoselectivity by the addition of ytterbium triflate (Yb(OTf)(3)) (10 mol %) in the rhodium(ll) acetate (Rh-2(OAc)(4))-catalyzed decomposition of o-(methoxycarbonyl)-alpha-diazoacetophenone in the presence of benzaldehyde. In the reaction in the absence of Yb(OTf)(3), almost no selectivity was obtained. Stereoselectivity in the reactions with p-nitrobenzaldehyde, p-anisaldehyde, and benzyloxyacetaldehyde could be also controlled to high exo preference by the addition of Yb(Otf)(3).
引用
收藏
页码：3145 / 3148
页数：4
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