Progress on the Synthesis of 1, 3-Amino Alcohol
- Corresponding author: Xiao Zufeng, chemhbeu@163.com Zhu Lei, lei.zhu@hbeu.edu.cn
Citation:
Wang Wei, Hu Yi, Lin Ruiqi, Wu Heng, Tong Qi, Wang Liansheng, Xiao Zufeng, Zhu Lei. Progress on the Synthesis of 1, 3-Amino Alcohol[J]. Chinese Journal of Organic Chemistry,
;2020, 40(5): 1129-1149.
doi:
10.6023/cjoc201911011
Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957.
doi: 10.1016/S0040-4020(02)00584-7
Lait, S. M.; Rankic, D. A.; Keay, B. A. Chem. Rev. 2007, 107, 767.
doi: 10.1021/cr050065q
(a) Davis, F. A.; Gaspari, P. M.; Nolt, B. M.; Xu, P. J. Org. Chem. 2008, 73, 9619.
(b) Shiro, Y.; Kato, K.; Fujii, M.; Ida, Y.; Akita, H. Tetrahedron 2006, 62, 8687.
(c) Aschwanden, P.; Kværnø, L.; Geisser, R. W.; Kleinbeck, F.; Carreira, E. M. Org. Lett. 2005, 7, 5741.
(d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
Yao, C.-Z.; Xiao, Z.-F.; Ning, X.-S.; Liu, J.; Zhang, X.-W.; Kang, Y.-B. Org. Lett., 2014, 16, 5824.
doi: 10.1021/ol502956j
Loh, T.-K.; Huang, J.-M.; Goh, S.-H.; Vittal, J. J. Org. Lett. 2000, 2, 1291.
doi: 10.1021/ol000042s
(a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518.
(b) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
Mackey, P.; Cano, R.; Foley, V. M.; McGlacken, G. P. Org. Synth. 2017, 94, 259.
doi: 10.15227/orgsyn.094.0259
(a) Kennedy, A.; Nelson, A.; Perry, A. Synlett 2004, 967.
(b) Fjelbey, K.; Svenstrup, N.; Püschl, A. Synthesis 2015, 47, 3231.
Enders, D.; Moser, M.; Geibel, G.; Laufer, M. C. Synthesis 2004, 2040.
List, B. J. Am. Chem. Soc. 2000, 122, 9336.
doi: 10.1021/ja001923x
(a) Cόrdova, A. Synlett 2003, 1651.
(b) Cόrdova, A. Chem. Eur. J. 2004, 10, 1987.
Westermann, B.; Neuhaus, C. Angew. Chem., Int. Ed. 2005, 44, 4077.
doi: 10.1002/anie.200500297
Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079.
doi: 10.1002/anie.200500810
Fustero, S.; Jiménez, D.; Moscardó, J.; Catalán, S.; Pozo, C. Org. Lett. 2007, 9, 5283.
doi: 10.1021/ol702447y
Jha, V.; Kondekar, N. B.; Kumar, P. Org. Lett. 2010, 12, 2762.
doi: 10.1021/ol100856u
Millet, R.; Träff, A. M.; Petrus, M. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 2010, 132, 15182.
doi: 10.1021/ja107857v
Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
doi: 10.1021/ja063267s
Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
doi: 10.1021/ja028353g
Frías, M.; Carrasco, A. C.; Fraile, A.; Alemán, J. Chem.-Eur. J. 2017, 23, 3117.
doi: 10.1002/chem.201605157
Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734.
doi: 10.1021/ja049388e
Matsunaga, S.; Yoshida, T.; Mornoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777.
doi: 10.1021/ja0482435
Trost, B. M.; Hung, C.-I.; Saget, T.; Gnanamani, E. Nat. Catal. 2018, 1, 523.
doi: 10.1038/s41929-018-0093-6
(a) Espino, C. G.; When, P. M.; Chow, J.; Bois, J. D. J. Am. Chem. Soc. 2001, 123, 6935.
(b) Fiori, K. W; Espino, C. G.; Brodsky, B. H.; Bois, J. D. Tetrahedron 2009, 65, 3042.
Fiori, K. W.; Fleming, J. J.; Bois, J. D. Angew Chem., Int. Ed. 2004, 43, 4349.
doi: 10.1002/anie.200460791
Alderson, J. M.; Schomaker, J. M. Chem. Eur. J. 2017, 23, 8571.
doi: 10.1002/chem.201702038
Zalatan, D. N.; Bois, J. D. J. Am. Chem. Soc. 2008, 130, 9220.
doi: 10.1021/ja8031955
Spreider, P. A.; Haydl, A.M.; Heinrich, M.; Breit, B. Angew. Chem. 2016, 128, 15798.
doi: 10.1002/ange.201609366
Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707.
doi: 10.1021/ja9054959
Qi, X.-B.; Rice, G. T.; Lall, M. S.; Plummer, M. S.; White, M. C. Tetrahedron 2010, 66, 4816.
doi: 10.1016/j.tet.2010.04.064
Nahra, E.; Liron, F.; Prestat, G.; Mealli, C.; Messaoudi, A.; Poli, G. Chem. Eur. J. 2009, 15, 11078.
doi: 10.1002/chem.200901946
Xie, Y.-Z., Yu, K.; Gu, Z.-H. J. Org. Chem. 2014, 79, 1289.
doi: 10.1021/jo402681z
Ma, R.; Young, J.; Promontorio, R.; Dannheim, F. M.; Pattillo, C. C.; White, M. C. J. Am. Chem. Soc. 2019, 141, 9468.
doi: 10.1021/jacs.9b02690
Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036.
doi: 10.1021/ja211600g
Ohno, H.; Hamaguchi, H.; Tanaka, T. J. Org. Chem. 2001, 66, 1867.
doi: 10.1021/jo005756v
Takemoto, Y.; Anzai, M.; Yanada, R.; Fujii, N.; Ohno, H.; Ibuka, T. Tetrahedron Lett. 2001, 42, 1725.
doi: 10.1016/S0040-4039(00)02334-0
Zhang, Y.-Q.; Bohle, F.; Bleith, R.; Schnakenburg, G.; Grimme, S.; Gansäuer, A. Angew. Chem. 2018, 130, 13716.
doi: 10.1002/ange.201808034
Liu, J.; Wang, C. ACS Catal. 2020, 10, 556.
doi: 10.1021/acscatal.9b04823
Ghorai, M. K.; Das, K.; Kumar, A. Tetrahedron Lett. 2007, 48, 4373.
doi: 10.1016/j.tetlet.2007.04.097
Singh, A.; Sharma, B.; Sachdeva, D.; Mehra, V.; Singh, P.; Kumar, V. ChemistrySelect 2018, 3, 4764.
doi: 10.1002/slct.201800512
Yao, C.-Z.; Xiao, Z.-F.; Liu, J.; Ning, X.-S.; Kang, Y.-B. Org. Lett. 2014, 16, 2498.
doi: 10.1021/ol500869p
Yao, C.-Z.; Xiao, Z.-F.; Ning, X.-S.; Liu, J.; Zhang, X.-W.; Kang, Y.-B. Org. Lett. 2014, 16, 5824.
doi: 10.1021/ol502956j
Xiao, Z.-F.; Yao, C.-Z.; Kang, Y.-B. Org. Lett. 2014, 16, 6512.
doi: 10.1021/ol503261h
Tiecco, M.; Testaferri, L.; Marini, F.; Sternativo, S.; Santi, C.; Bagnoli, L.; Temperini, A. Tetrahedron: Asymmetry 2001, 12, 3053.
doi: 10.1016/S0957-4166(01)00543-2
(a) Gais, H.-J.; Loo, R.; Das, P.; Raabe, G. Tetrahedron Lett. 2000, 41, 2851.
(b) Gais, Hans-Joachim; Loo, R.; Roder, D.; Das, P.; Raabe, G. Eur. J. Org. Chem. 2003, 1500.
Murai, T.; Sano, H.; kawai, H.; Aso, H.; Shibahara, F. J. Org. Chem. 2005, 70, 8148.
doi: 10.1021/jo051378o
Daniel, P. E.; Weber, A. E.; Malcolmson, S. J. Org. Lett. 2017, 19, 3490.
doi: 10.1021/acs.orglett.7b01471
Geng, H.; Zhang W.; Chen, J.; Hou, G.; Zhou, L.; Zou, Y.; Wu, W.; Zhang, X. Angew. Chem., Int. Ed. 2009, 48, 6052.
doi: 10.1002/anie.200902339
Xi, Y.; Butcher, T. W.; Zhang, J.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 776.
doi: 10.1002/anie.201509235
Ying, J.; Pu, L. J. Org. Chem. 2016, 81, 8135.
doi: 10.1021/acs.joc.6b01111
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni3N supported Al-doped SrTiO3: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO2 hydrogenation over a Mg-doped In2O3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H2 production activity of BaTiO3 nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
Xiaofang Li , Zhigang Wang . Modulating dz2-orbital occupancy of Au cocatalysts for enhanced photocatalytic H2O2 production. Acta Physico-Chimica Sinica, 2025, 41(7): 100080-. doi: 10.1016/j.actphy.2025.100080
Jun LI , Huipeng LI , Hua ZHAO , Qinlong LIU . Preparation and photocatalytic performance of AgNi bimetallic modified polyhedral bismuth vanadate. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 601-612. doi: 10.11862/CJIC.20230401
Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO4:Yb3+,Er3+ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co3O4 as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402