Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed "interrupted" Feist-Benary reaction
Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed "interrupted" Feist-Benary reaction
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DOI：
10.1016/j.cclet.2009.10.012
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发表时间：
2010-02-01
影响因子：
9.1
通讯作者：
Zhang, Sheng Yong
中科院分区：
文献类型：
--
作者：
Chen, Hui;Jiang, Ru;Zhang, Sheng Yong
本文合成了六个9-nat和9-epi构型的金鸡纳碱硫脲衍生物。在结构表征后，我们将其用于α-卤代酮与β-二羰基化合物的不对称“中断”Feist-Benary（IFB）反应，得到光学活性的二氢呋喃。考察了各种硫脲衍生物作为有机催化剂的性能。相应的手性羟基二氢呋喃类化合物以优异的产率和中等的ee得到。对于无环底物，我们得到了令人兴奋和有希望的结果。(C)2009年张盛勇。Elsevier B. V.代表中国化学会出版。All rights reserved.
In this study, six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi-configuration were synthesized. After characterized the structures, we adopted them to the asymmetric "interrupted" Feist-Benary (IFB) reaction of alpha-haloketones with beta-dicarbonyl compounds, to give optically active dihydrofurans. Various thiourea derivatives as organocatalysts were examined. The corresponding chiral hydroxyl dihydrofurans have been obtained in excellent yields and moderate ees. To the acyclic substrate, we obtained exciting and promising result. (C) 2009 Sheng Yong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.