2-Amino homopropargyl alcohols from the highly regioselective Ag2CO3-catalyzed nucleophilic openings of alkynyl epoxides by amines
- Corresponding author: Ruwei Shen, shenrw@njtech.edu.cn; srw1100@hotmail.com
Citation:
Yang Jianlin, Zhang Ming, Wang Peng, Liu Wenjuan, Ruwei Shen. 2-Amino homopropargyl alcohols from the highly regioselective Ag2CO3-catalyzed nucleophilic openings of alkynyl epoxides by amines[J]. Chinese Chemical Letters,
;2018, 29(3): 524-526.
doi:
10.1016/j.cclet.2017.09.001
C. Gronnier, S. Kramer, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 134(2012) 828-831.
doi: 10.1021/ja209866a
A. Fürstner, E. Kattnig, O. Lepage, J. Am. Chem. Soc. 128(2006) 9194-9204.
doi: 10.1021/ja061918e
C.Z. Rotsides, C. Hu, K.A. Woerpel, Angew. Chem. Int. Ed. 52(2013) 13033-13036.
doi: 10.1002/anie.201306093
(a) C. Deutsch, A. Hoffmann-Roder, A. Domke, N. Krause, Synlett 5(2007) 737-740;
(b) M. Yoshida, M. Hayashi, K. Shishido, Org. Lett. 9(2007) 1643-1646;
(c) T. Miura, M. Shimada, S. Y. Ku, T. Tamai, M. Murakami, Angew. Chem. Int. Ed. 46(2007) 7101-7103;
(d) T. Miura, M. Shimada, P. de Mendoza, et al., J. Org. Chem. 74(2009) 6050-6054;
(e) N. K. Ratmanova, D. S. Belov, A. Andreev, A. V. Kurkin, Tetrahedron: Asymmetry 25(2014) 468-472;
(f) J. L. Chen, F. Zheng, Y. Huang, F. L. Qing, J. Org. Chem. 76(2011) 6525-6533;
(g) J. Zhao, K. J. Szabó, Angew. Chem. Int. Ed. 55(2016) 1502-1506;
(h) T. S. N. Zhao, Y. Yang, T. Lessing, K. J. Szabó, J. Am. Chem. Soc. 136(2014) 7563-7566.
(a) M. Chini, P. Crotti, F. Macchia, J. Org. Chem. 56(1991) 5939-5942;
(b) J. Auge, F. Leroy, Tetrahedron Lett. 37(1996) 7715-7716;
(c) M. Chini, P. Crotti, L. Favero, F. Macchia, M. Pineschi, Tetrahedron Lett. 35(1994) 433-436;
(d) K. Fagnou, M. Lautens, Org. Lett. 2(2000) 2319-2321;
(e) G. Sekar, V. K. Singh, J. Org. Chem. 64(1999) 287-289;
(f) J. S. Yadav, A. Bandyopadhyay, B. V. S. Reddy, Tetrahedron Lett. 42(2001) 6385-6388.
(a) V. M. Albitskaya, E. M. Blyakhman, A. A. Petrov, Zh. Obshch. Khim. 30(1960) 2267-2269;
(b) L. N. Shil'nikova, F. Y. Perveev, Zh. Organicheskoi Khim. 14(1978) 251-256.
(a) M. Chini, P. Crotti, F. Macchia, Tetrahedron Lett. 31(1990) 4661-4664;
(b) I. A. Andreev, D. S. Belov, A. V. Kurkin, M. A. Yurovskaya, Eur. J. Org. Chem. 2013(2013) 649-652;
(c) D. S. Belov, E. R. Lukyanenko, A. V. Kurkin, M. A. Yurovskaya, J. Org. Chem. 77(2012) 10125-10134.
G. Hattori, A. Yoshida, Y. Miyake, Y. Nishibayashi, J. Org. Chem. 74(2009) 7603-7607.
doi: 10.1021/jo901064n
(a) R. Shen, J. Yang, M. Zhang, L. B. Han, Adv. Synth. Catal. (2017), doi: http://dx.doi.org/10.1002/adsc.201700421;
(b) R. Shen, J. Yang, H. Zhao, et al., Chem. Comm. 52(2016) 11959-11962;
(c) R. Shen, B. Luo, J. Yang, L. Zhang, L. B. Han, Chem. Comm. 52(2016) 6451-6454;
(d) R. Shen, J. Yang, B. Luo, L. Zhang, L. B. Han, Adv. Synth. Catal. 358(2016) 3897-3906.
S.M. Lait, D.A. Rankic, B.A. Keay, Chem. Rev. 107(2007) 767-796.
doi: 10.1021/cr050065q
A. Blanc, A. Alix, J.M. Weibel, P. Pale, Eur. J. Org. Chem. 2010(2010) 1644-1647.
doi: 10.1002/ejoc.v2010:9
Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF3·OEt2-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
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
Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
Wenya Jiang , Jianyu Wei , Kuan-Guan Liu . Atomically precise superatomic silver nanoclusters stabilized by O-donor ligands. Chinese Journal of Structural Chemistry, 2024, 43(9): 100371-100371. doi: 10.1016/j.cjsc.2024.100371
Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
Zongyi Huang , Cheng Guo , Quanxing Zheng , Hongliang Lu , Pengfei Ma , Zhengzhong Fang , Pengfei Sun , Xiaodong Yi , Zhou Chen . Efficient photocatalytic biomass-alcohol conversion with simultaneous hydrogen evolution over ultrathin 2D NiS/Ni-CdS photocatalyst. Chinese Chemical Letters, 2024, 35(7): 109580-. doi: 10.1016/j.cclet.2024.109580
Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
Jie Ren , Hao Zong , Yaqun Han , Tianyi Liu , Shufen Zhang , Qiang Xu , Suli Wu . Visual identification of silver ornament by the structural color based on Mie scattering of ZnO spheres. Chinese Chemical Letters, 2024, 35(9): 109350-. doi: 10.1016/j.cclet.2023.109350
Ya-Wen Zhang , Ming-Ming Gan , Li-Ying Sun , Ying-Feng Han . Supramolecular dinuclear silver(I) and gold(I) tetracarbene metallacycles and fluorescence sensing of penicillamine. Chinese Journal of Structural Chemistry, 2024, 43(9): 100356-100356. doi: 10.1016/j.cjsc.2024.100356