Citation:
Ai Qiao MI, Zeng Xin MA, Lan Jun WU, Yao Zhong JIANG. ASYMMETRIC SYNTHESIS Ⅻ:HIGHLY ENANTIOSELECTIVE SYNTHESIS OF α-AMINO ACIDS BY ALKYLATION OF THE KETIMINE FROM 2-HYDROXY-PINAN-3-ONE AND MENTHYL GLYCIN-ATE A DOUBLE ASYMMETRIC INDUCTION SYSTEM[J]. Chinese Chemical Letters,
;1991, 2(2): 115-118.
-
A series of α-amino acids are obtained in 72-96% optical yields by alkylation of the ketimine derived from (+)-2-hydroxy-pinan-3-one and (-)-menthyl glycinate followed by hydrolysis of the alkylated intermediates with mineral acid. The double asymmetric induction are explained by the transition model of lithium enolate.
-
-
-
-
[1]
Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
-
[2]
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
-
[3]
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
-
[4]
Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
-
[5]
Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
-
[6]
Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
-
[7]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[8]
Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
-
[9]
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
-
[10]
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
-
[11]
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
-
[12]
Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
-
[13]
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
-
[14]
Lanfang Wang , Jiangnan Lv , Yujia Li , Yanqing Hao , Wenjiao Liu , Hui Zhang , Xiaohong Xu . One-step synthesis of nanowoven ball-like NiS-WS2 for high-efficiency hydrogen evolution. Chinese Chemical Letters, 2025, 36(1): 109597-. doi: 10.1016/j.cclet.2024.109597
-
[15]
Ting Xie , Xun He , Lang He , Kai Dong , Yongchao Yao , Zhengwei Cai , Xuwei Liu , Xiaoya Fan , Tengyue Li , Dongdong Zheng , Shengjun Sun , Luming Li , Wei Chu , Asmaa Farouk , Mohamed S. Hamdy , Chenggang Xu , Qingquan Kong , Xuping Sun . CoSe2 nanowire array enabled highly efficient electrocatalytic reduction of nitrate for ammonia synthesis. Chinese Chemical Letters, 2024, 35(11): 110005-. doi: 10.1016/j.cclet.2024.110005
-
[16]
Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
-
[17]
Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na3V2(PO4)3 cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
-
[18]
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
-
[19]
Jinglin CHENG , Xiaoming GUO , Tao MENG , Xu HU , Liang LI , Yanzhe WANG , Wenzhu HUANG . NiAlNd catalysts for CO2 methanation derived from the layered double hydroxide precursor. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1592-1602. doi: 10.11862/CJIC.20240152
-
[20]
Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
-
[1]
Metrics
- PDF Downloads(2)
- Abstract views(525)
- HTML views(0)