Citation: Jiang Quan, He Ling, Li Weidong. Studies on the Stereoselective Synthesis of Functionalized Allylsilane Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3454-3459. doi: 10.6023/cjoc201904081 shu

Studies on the Stereoselective Synthesis of Functionalized Allylsilane Compounds

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331

Corresponding author: He Ling, heling2015@cqu.edu.cn Li Weidong, wdli@cqu.edu.cn
Received Date: 30 April 2019
Revised Date: 25 July 2019
Available Online: 30 December 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21672030, 21702023)the National Natural Science Foundation of China 21672030the National Natural Science Foundation of China 21702023

Figures(4)

Allylsilanes have emerged as synthetically useful intermediates that can undergo a variety of chemical transformations and have been found versatile applications in C-C bond construction as well as in preparation of complex molecules. Exploration on the stereoselective route to functionalized allylsilanes is of great significance for the development of organic synthetic methodology. An efficient pathway to a series of novel alkoxy-substituted homoiodio-allylsilanes via the Julia olefination of silylmethyl cyclopropyl carbinols was described. Carbinols derived from cyclopropyl aryl ketone were evidenced to be superiorer in controlling the stereoselectivity of the products than the alkyl equivalents.
- allylsilane,
- Julia olefination,
- cyclopropyl carbinol,
- Grignard reagent
1. [1]
  Sommer, L. H.; Tyler, L. J.; Whitmore, F. C. J. Am. Chem. Soc. 1948, 70, 2872. doi: 10.1021/ja01189a010
2. [2]
  For recent reviews, see: (a) Ramachandran, P. V.; Nicponski, D. R.; Gagare, P. D. In Comprehensive Organic Synthesis II, Vol. 2, Eds.: Knochel, P.; Molander, G. A., Elsevier, Amsterdam, 2014, p. 72.
  (b) Díez-Poza, C.; Barbero, A. Eur. J. Org. Chem. 2017, 2017, 4651.
  (c) Schmidt, A. W.; Knölker, H.-J. Synlett 2010, 2207.
  (d) Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173.
  (e) Barbero, A.; Pulido, F. J. Acc. Chem. Res. 2004, 37, 817.
  (f) Méndez, M.; Echavarren, A. M. Eur. J. Org. Chem. 2002, 15.
  (g) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
3. [3]
  Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375. doi: 10.1021/cr00037a011
4. [4]
  For reviews on the synthesis of allylsilanes see 2a, and also see: (a) Sarkar, T. K. Synthesis 1990, 969.
  (b) Sarkar, T. K. Synthesis 1990, 1101.
  (c) Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 680, 43.
  (d) Barbero, A.; Pulido, F. J. Synthesis 2004, 779.
5. [5]
  Han, J. W.; Hayashi, T. Tetrahedron: Asymmetry 2010, 21, 2193 and references therein. doi: 10.1016/j.tetasy.2010.07.034
6. [6]
7. [7]
  (a) Li, W.-D. Z.; Yang, J.-H. Org. Lett. 2004, 6, 1849.
  (b) Yang, J. H.; Li, W. D. Z. Chin. Chem. Lett. 2005, 16, 433.
8. [8]
  (a) Shen, S.-J.; Li, W.-D. Z. J. Org. Chem. 2013, 78, 7112.
  (b) Gao, H.-T.; Wang, B.-L.; Li, W.-D. Z. Tetrahedron 2014, 70, 9436.
9. [9]
  Li, W.-D. Z.; Peng, Y. Org. Lett. 2005, 7, 3069. doi: 10.1021/ol051051+
10. [10]
  Lawrence, N. J. Science of Synthesis (Houben-Weyl), Georg Thieme Verlag, Stuttgart, Germany, 2002, pp. 579~594.
11. [11]
  Methoxymethyl magnesium chloride is known to be obtained at low temperature but decomposes above -20℃ to release ethylene gas, see: (a) Normant, H.; Castro, B. C. R. Acad. Sci. 1963, 257, 2115.
  (b) Castro, B. Bull. Soc. Chim. Fr. 1967, 1533.
12. [12]
  Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943. doi: 10.1021/jo0498866
1. [1]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
2. [2]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
3. [3]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
4. [4]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
5. [5]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055
6. [6]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
7. [7]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
8. [8]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
9. [9]
  Hongling Yuan , Jialin Xie , Jiawei Wang , Jixiang Zhao , Jiayan Liu , Qing Feng , Wei Qi , Min Liu . Cyclic Olefin Copolymer (COC): The Agile Vanguard in the Realm of Materials. University Chemistry, 2024, 39(7): 294-298. doi: 10.12461/PKU.DXHX202311041
10. [10]
  Jiamin Li , Wenyue Zhong , Kin Shing Chan . “烯”君入瓮又入学——据元素周期表与酸碱理论谈烯烃教学. University Chemistry, 2025, 40(6): 177-182. doi: 10.12461/PKU.DXHX202408040
11. [11]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
12. [12]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
13. [13]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
14. [14]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
15. [15]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
16. [16]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
17. [17]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
18. [18]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
19. [19]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
20. [20]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(628)
HTML views(56)

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