Citation: Jian Feng Xu, Peng Bin Li, Lu Ling Wu, Xian Huang. Regio- and stereo-selective synthesis of multi-substituted 3-pyrrolines[J]. Chinese Chemical Letters, ;2009, 20(9): 1015-1016. doi: 10.1016/j.cclet.2009.04.037 shu

Regio- and stereo-selective synthesis of multi-substituted 3-pyrrolines

a Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, China;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received Date: 24 December 2008

Fund Project: We are grateful to the National Natural Science Foundation of China (No.20672095) and CAS Academician Foundation of Zhejiang Province for financial support.

A regio- and stereo-selective synthesis of multi-substituted 3-pyrrolines has been developed. The multi-substituted 3-pyrrolines were synthesized in good yields by 1,3-dipolar cycloaddition of methyl 2-(phenylselanyl)acrylate with azomethine ylides, followed by N-acylation and oxidation-elimination of phenylseleno group.
- 3-Pyrrolines,
- 1,3-Dipolar cycloaddition,
- Regioselective,
- Stereoselective
1. [1]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
2. [2]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
3. [3]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
4. [4]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
5. [5]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
6. [6]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
7. [7]
  Junhua Li , Tianci Shen , Yahui Zhuang , Yu Fu , Yian Shi . Pd-Catalyzed highly regioselective migratory hydroesterification of internal olefins with formates. Chinese Chemical Letters, 2025, 36(7): 110599-. doi: 10.1016/j.cclet.2024.110599
8. [8]
  He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076
9. [9]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
10. [10]
  Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
11. [11]
  Zhihua Wang , Xiang-Zhao Zhu , Xinglei He , Chen-Xu Gong , Wang-Fu Liang , Wenfeng Wang , Yuqi Lin , Ke-Yin Ye . Deoxygenative hydrohalogenation of propargyl alcohols: Regio- and stereoselective synthesis of unsaturated distal dihalides. Chinese Chemical Letters, 2025, 36(12): 111067-. doi: 10.1016/j.cclet.2025.111067
12. [12]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
13. [13]
  Yaqi Deng , Jian Xue , Xiang Wu , Shunying Liu . Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles. Chinese Chemical Letters, 2025, 36(9): 110822-. doi: 10.1016/j.cclet.2025.110822
14. [14]
  Junyou Ding , Xiaotong Li , Hongmin Lin , Bochao Ye , Xing Zhou , Feihu Cui , Yingming Pan , Haitao Tang . Highly regioselective hydrogermylation of unsaturated C-C bonds over ligand-control single atom palladium catalysts. Chinese Chemical Letters, 2025, 36(11): 111286-. doi: 10.1016/j.cclet.2025.111286
15. [15]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
16. [16]
  Kexiang Zhao , Zongrui Wang , Qi-Yuan Wan , Jing-Cai Zeng , Li Ding , Jie-Yu Wang , Jian Pei . Janus-type BN-embedded perylene diimides via a "shuffling" strategy: Regioselective functionalizable building block towards high-performance n-type organic semiconductors. Chinese Chemical Letters, 2025, 36(6): 110339-. doi: 10.1016/j.cclet.2024.110339
17. [17]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
18. [18]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
19. [19]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
20. [20]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1213)
HTML views(51)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return