Scope and diastereoselectivity of the "interrupted" Feist-Benary reaction
Scope and diastereoselectivity of the "interrupted" Feist-Benary reaction
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DOI：
10.1021/ol0169978
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发表时间：
2002-01-24
期刊：
影响因子：
5.2
通讯作者：
Zhu, C
中科院分区：
文献类型：
--
作者：
Calter, MA;Zhu, C
β-二羰基化合物与α-卤代酮的碱促进缩合，即Feist-Benary反应，可以方便地产生高度取代的二氢呋喃。我们在这里表明，这个反应是相当普遍的β-二羰基化合物的性质，进行β-酮酯，β-氧代丙酸酯，β-二酮，和β-二醛。我们还表明，该反应的非对映选择性取决于亲核试剂的酸度。
[GRAPHICS]The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Benary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.