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 shu

Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction

a Department of Chemistry, Fourth Military Medical University, Xi'an 710032, China;
b Department of Shannxi Institute for Food and Drug Control, Xi'an 710061, China

Received Date: 25 June 2009

Fund Project: We thank the National Natural Science Foundation of China (Nos. 20572131, 20372083, 20972189, 20672141, 30901883).

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.
- Interrupted Feist-Bénary (IFB) reaction,
- Chital,
- Thiourea,
- Dihydrofuran
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