“中断的”费斯特-贝纳里反应的范围和非对映选择性。

Scope and diastereoselectivity of the "interrupted" Feist-Bénary reaction.

作者信息

Calter Michael A, Zhu Cheng

机构信息

Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.

出版信息

Org Lett. 2002 Jan 24;4(2):205-8. doi: 10.1021/ol0169978.

DOI:10.1021/ol0169978

PMID:11796051

Abstract

[reaction: see text] The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Bénary 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.

摘要

[反应：见正文] β-二羰基化合物与α-卤代酮在碱促进下的缩合反应，即费斯特-贝纳里反应，可方便地生成高度取代的二氢呋喃。我们在此表明，就β-二羰基化合物的性质而言，该反应具有相当的普遍性，β-酮酯、β-氧代丙酸酯、β-二酮和β-二醛均可发生此反应。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。