Synthesis of a New Kind of Chiral Alkylaminobenzylphe-nol/naphthol Ligands

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Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (04): 465-469. Previous Articles Next Articles

Original Articles

一类新型手性烷基氨基酚类配体的合成

李志敏，孙岩，申秀民，艾林，张聪*

(北京师范大学化学学院北京 100875)

收稿日期:2005-02-05 修回日期:2005-10-24 发布日期:2006-03-31
通讯作者: 张聪

Synthesis of a New Kind of Chiral Alkylaminobenzylphe-nol/naphthol Ligands

LI Zhi-Min,SUN Yan,SHEN Xiu-Min,AI Lin,ZHANG Cong*

(College of Chemistry, Beijing Normal University, Beijing 100875)

Received:2005-02-05 Revised:2005-10-24 Published:2006-03-31

Contact: ZHANG Cong

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Abstract

A new kind of chiral alkylaminobenzylphenol/naphthol was enantioselectively synthesized with moderate yield for the first time through Mannich reaction. Their structures were characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR and MS spectra, two of which were identified through X-ray crystallography study.

Key words: enantioselectivity, chiral synthesis, Mannich reaction

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LI Zhi-Min,SUN Yan,SHEN Xiu-Min,AI Lin,ZHANG Cong*. Synthesis of a New Kind of Chiral Alkylaminobenzylphe-nol/naphthol Ligands[J]. Chin. J. Org. Chem., 2006, 26(04): 465-469.

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[1] Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.

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[14] Song, Xiaoli ; Yan, Jufang; Fan, Li; Chen, Xin;
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[1]	Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.
[2]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[3]	Zhang Shiju, Li Xiaotong, Wang Yan, Zheng Yucong, Han Shiqing, Yu Huilei, Huang Shahua. Formal Synthesis of Gram-Negative Antibiotic Negamycin [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 521-527.
[4]	Ye Jianliang, Huang Peiqiang. Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids [J]. Chin. J. Org. Chem., 2018, 38(9): 2215-2230.
[5]	Liu Yuting, Wu Qianqian, Yin Dawei, Li Diyang. Latest Progress and Application of Mannich Reaction [J]. Chin. J. Org. Chem., 2016, 36(5): 927-938.
[6]	Hui Yonghai, Shi Wei, Xie Shaolei, Wang Changchun, Xie Zhengfeng. Three-Component Mannich Reaction Catalyzed by MCM-41 Immobilized H₃PW₁₂O₄₀ (PW) in Water [J]. Chin. J. Org. Chem., 2014, 34(6): 1212-1217.
[7]	Liu Zhichang, Wang Yinghong, Zeng Hongyao, Nie Wanli, Xiang Qingxiang. Synthesis and Antibacterial Activities of Mannich Bases of Curcumin Derivatives [J]. Chin. J. Org. Chem., 2014, 34(11): 2345-2349.
[8]	LIU Wen-Jun, WANG Xin, LI Gang, YE Jia, CHENG Tie-Ming, LI Run-Tao. Synthesis and Analgesic Activity of Mono-spirocyclopiperazinium Analogues [J]. Chin. J. Org. Chem., 2011, 31(12): 2135-2139.
[9]	CHEN Jun-Li, JIE Zheng-Feng, XING Ye. Mannich Reaction of Acetophenone, Aromatic Aldehydes and Aro-matic Amines Catalyzed by Tungstophosphoric Acid in Water [J]. Chin. J. Org. Chem., 2011, 31(10): 1714-1718.
[10]	ZHANG Ping, HUANG Jin-Hua, WANG Lan-Zhi, LIU Wei, LI Yuan. Synthesis of Methyl 4-Substituted-phenyl-2,3-dihydro-1,5- benzothi-azepine-3-acetates and Their Sodium Salts [J]. Chin. J. Org. Chem., 2010, 30(12): 1939-1943.
[11]	ZHOU Jie-Wen, YAN Ju-Fang, TANG Xue-Mei, ZHANG Wei-Yu, ZHANG Yang-Xia, CHEN Xin, SU Xiao-Yan, YANG Da-Cheng. Synthesis and Preliminary Evaluation of Antidiabetic Activity for β-Amino Ketone Containing Isoxazole Moiety [J]. Chin. J. Org. Chem., 2010, 30(04): 582-589.
[12]	LI Qing-Xia, WANG Feng, MENG Wen-Jun, MENG Zi-Hui, LOU Zhong-Liang, SONG Gong-Yan, QIN Guang-Meng, GE Zhong-Hua, WANG Bo-Zhou. Reaction Mechanism for the Formation of 1,3-Ditertiobutyl-5,5- dinitrohexahydropyrimidine [J]. Chin. J. Org. Chem., 2010, 30(03): 409-413.
[13]	WANG Min, LIANG Yan, SONG Zhi-Guo, JIANG Heng. Efficient One-Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Aluminium p-Toluenesulfonate under Mild Conditions [J]. Chin. J. Org. Chem., 2010, 30(02): 295-298.
[14]	Song, Xiaoli ; Yan, Jufang; Fan, Li; Chen, Xin; Xu, Jin ; Zhou, Zuwen; Yang, Dacheng* . Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(1-Aryl-3-aryl/arylalkyl-3-oxopropylamino)-N-(5-methyl- 3-isoxazolyl)benzene Sulfonamide [J]. Chin. J. Org. Chem., 2009, 29(04): 606-613.
[15]	XU Qi-Gui^a,LIU Tian-Yu^a,TIAN Rui^a,MA De-Yin^b,LI Qin-Geng*^,a. Synthesis and Antiemetic Activity of 3-(4-Substituted-piperazin-1- yl-methyl)-1,2,3,9-tetrahydrocarbazol-4-one Derivatives [J]. Chin. J. Org. Chem., 2008, 28(2): 234-239.