Synthesis of Sulfur-Containing Chiral jS-Amino Alcohols and Their Application in the Enantioselective Reduction of Prochiral Ketones

Chin. J. Org. Chem. ›› 2003, Vol. 23 ›› Issue (12): 1393-1395. Previous Articles Next Articles

含流手性β-氨基醇的合成及其在对映选择性还原反应中的应用

陈维一;陆军;蒋虹;钱荣;沈宗旋;张雅文

苏州大学化学化工学院

发布日期:2003-12-25

Synthesis of Sulfur-Containing Chiral jS-Amino Alcohols and Their Application in the Enantioselective Reduction of Prochiral Ketones

Chen Weiyi;Lu Jun;Jiang Hong;Qian Rong;Shen Zongxuan;Zhang Yawen

Department of Chemistry and Chemical Engineering,Suzhou University

Published:2003-12-25

Abstract

Three novel sulfur-containing chiral β-amino alcohols 4a - 4c have been prepared from S-alkylated L-cysteine 2a - 2c. These compounds could be used as catalysts in the enantioselective reduction of prochiral ketones with the NaBH_4/I_2 system. The optically active secondary alcohols were obtained in moderate to high enantiomeric excesses and high chemical yields.

Key words: AMINO ALCOHOL, REDUCTION, SELECTIVITY, CYSTEINE, KETONE, ESTERIFICATION

CLC Number:

O621

Cite this article

Chen Weiyi;Lu Jun;Jiang Hong;Qian Rong;Shen Zongxuan;Zhang Yawen. Synthesis of Sulfur-Containing Chiral jS-Amino Alcohols and Their Application in the Enantioselective Reduction of Prochiral Ketones[J]. Chin. J. Org. Chem., 2003, 23(12): 1393-1395.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[2]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[3]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[4]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[5]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[6]	Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.
[7]	Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou. Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2855-2863.
[8]	Xiangping Chen, Chenxiang Meng, Mengna Li, Shangmin Chu, Xinxin Zhu, Kai Xu, Lantao Liu, Tao Wang, Fenghua Zhang, Fei Li. Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2800-2807.
[9]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[10]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[11]	Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505.
[12]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[13]	Feiran Liu, Jing Jing, Xiaoling Zhang. Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2053-2067.
[14]	Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.
[15]	Miaomiao Zhang, Rong Chen, Hongmei Jiao, Haojie Ma, Bo Han, Yuqi Zhang, Jijiang Wang. MgCl₂-Catalyzed Chemoselective Reduction of Aldehydes, Ketones and Imines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1462-1471.

含流手性β-氨基醇的合成及其在对映选择性还原反应中的应用

Synthesis of Sulfur-Containing Chiral jS-Amino Alcohols and Their Application in the Enantioselective Reduction of Prochiral Ketones

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments