A concise and stereospecific one-shot synthesis of bicyclo[3.3.1]nonenols from dimethyl 1,3-acetonedicarboxylate and enals via the sequential Michael addition - Intramolecular aldolization

被引：26

作者：

Aoyagi, K ^{[1
]}

Nakamura, H ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 11期

关键词：

D O I：

10.1021/jo9903306

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of dimethyl 1,3-acetonedicarboxylate 1 with enals 2 proceeded very smoothly in the presence of a catalytic amount of tetrabutylammonium fluoride or piperidine in THF at room temperature, giving the corresponding bicyclo[3.3.1]nonane derivatives 3 in high yields. Both of the two fused rings of 3 are newly constructed from the starting two acyclic substrates via the sequential Michael addition-intramolecular aldolization in one shot.

引用

页码：4148 / 4151

页数：4

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