引用本文:
Hui Chen, Ru Jiang, Qiao Feng Wang, Xiao Li Sun, Jing Luo, Sheng Yong Zhang. Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction[J]. Chinese Chemical Letters,
2010, 21(2): 167-170.
doi:
10.1016/j.cclet.2009.10.012
Citation: Hui Chen, Ru Jiang, Qiao Feng Wang, Xiao Li Sun, Jing Luo, Sheng Yong Zhang. Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction[J]. Chinese Chemical Letters, 2010, 21(2): 167-170. doi: 10.1016/j.cclet.2009.10.012
Citation: Hui Chen, Ru Jiang, Qiao Feng Wang, Xiao Li Sun, Jing Luo, Sheng Yong Zhang. Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction[J]. Chinese Chemical Letters, 2010, 21(2): 167-170. doi: 10.1016/j.cclet.2009.10.012
Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction
摘要:
In this study,six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi-conflguration were synthesized.After characterized the structures,we adopted them to the asymmetric "interrupted" Feist-Bénary (IFB) reaction of α-haloketones with β-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.
English
Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction
Abstract:
In this study,six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi-conflguration were synthesized.After characterized the structures,we adopted them to the asymmetric "interrupted" Feist-Bénary (IFB) reaction of α-haloketones with β-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.
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Key words:
- Interrupted Feist-Bénary (IFB) reaction
- / Chital
- / Thiourea
- / Dihydrofuran
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