Synthesis, Property and Application of 5-Alkoxy-2,5-dihydrofu-ran-2-ones

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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (03): 239-253. Next Articles

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γ-烷氧基-2(5H)-呋喃酮的合成、反应性及在合成中的应用

黄海波¹，齐传民*^,1，田作林²

(¹北京师范大学化学系北京 100875)
(²长春理工大学材料与工程学院长春 130022)

收稿日期:2003-12-23 修回日期:2004-07-01 发布日期:2005-02-28
通讯作者: 齐传民

Synthesis, Property and Application of 5-Alkoxy-2,5-dihydrofu-ran-2-ones

HUANG Hai-Bo¹,QI Chuan-Min*^,1,TIAN Zuo-Lin²

(¹ Department of Chemistry, Beijing Normal University, Beijing 100875)
(² School of Materials & Engineering, Changchun University of Science and Technology, Changchun 130022)

Received:2003-12-23 Revised:2004-07-01 Published:2005-02-28

Contact: QI Chuan-Min

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Abstract

The recent advance in synthesis, property and application of a new class of auxiliary based chiral synthons, 5-alkoxy-2,5-dihydrofuran-2-ones, is reviewed. The multifunctional compounds perform a varity of asymmetric transformations, Michael addition, cycloaddition and being attack at -position, and exhibit excellent convenience in asymmetric synthesis.

Key words: 5-alkoxy-2,5-dihydrofuran-2-one, cycloaddition, asymmetric syn-thesis, Michael addition

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HUANG Hai-Bo,QI Chuan-Min*^,1,TIAN Zuo-Lin^{2. Synthesis, Property and Application of 5-Alkoxy-2,5-dihydrofu-ran-2-ones[J]. Chin. J. Org. Chem., 2005, 25(03): 239-253.}

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[1]	Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.
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[3]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[4]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[5]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[6]	Deliang Kong, Wen Dai, Yiling Zhao, Yilin Chen, Hongping Zhu. Study on Oxidative Cycloaddition Reactions of Amidinatoboryl-aminosilylenes toward Ketone and Diketone Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1843-1851.
[7]	Fang Wei, Xin Yu, Qiang Xiao. Advances in C—N₃ Retention Reactions Involving Organic Azides [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1365-1385.
[8]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[9]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[10]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.
[11]	Junxiu Liang, Yazhou Liu, Amu Wang, Yanchao Wu, Xiaofeng Ma, Huijing Li. Dearomatization of Halonaphthols via an Intermolecular [4＋1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3888-3899.
[12]	Weilu Zhang, Shaowei Chen, Xiao Shen. Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3635-3643.
[13]	Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.
[14]	Changming Dong, Yi Xie, Guangxin Liang. A Feasible Route to Access the ABD Skeleton in Azadirachtin-Type Limonoids [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2857-2866.
[15]	Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.