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

页码：3145 / 3148

页数：4

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