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A Concise, Practical Chiral Resolution Approach of Racemic (E)-4,4-Dimethyl-1-(4-nitrophenyl)pent-1-en-3-ol to Its both Enantiomers via Strategy of Diastereomeric Ester Formation and Crystallization Using both N-Boc-D- and N-Boc-L-phenylglycines as Chiral Auxiliaries

文献类型：期刊论文

作者Jiang, Shanshan3,4; Yuan, Jia3,4; Qin, Yanlan3; Luo, Ying1,3; Jin, Zhengsheng3; Zhao, Guilong2,3; Ti, Huihui4
刊名CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
出版日期2024-04-25
页码10
关键词Chiral resolution Phenylglycine Chiral auxiliary Chiral secondary alcohol Diastereomeric ester formation
ISSN号1005-9040
DOI10.1007/s40242-024-4011-y
通讯作者Zhao, Guilong(zhao_guilong@126.com) ; Ti, Huihui(tihuihui@gdpu.edu.cn)
英文摘要Chiral secondary alcohols are an important class of functionalities commonly seen in drugs and other bioactive compounds. In an ongoing drug discovery program in our laboratories, a nitro-bearing racemic allylic secondary alcohol (+/-)-1 was discovered as a promising drug candidate, and in the following preclinical studies, a concise, reliable, practical synthetic approach to its both enantiomers with high optical purities was greatly needed. In the present study, we developed a chiral resolution approach of (+/-)-1 to its both enantiomers, i. e., (+)-1 and (-)-1, via the strategy of diastereomeric ester formation and crystallization using both N-Boc-D- and N-Boc-L-phenylglycines as chiral auxiliaries. The absolute configurations of all the four key intermediates were unambiguously determined by single-crystal X-ray diffraction, providing a solid foundation for the stereochemistry of the present study. The two enantiomers were obtained in high optical purities. This approach is characterized by scalability and practicality and is envisaged to enable the chiral resolution of other racemic secondary alcohols, especially those with labile groups, such as NO2 and olefinic C=C bond.
WOS关键词TOLYLACETIC-ACID CFTA ; KETONES
资助项目Guangdong Basic and Applied Basic Research Foundation, China[2021A1515010197] ; Guangdong Basic and Applied Basic Research Foundation, China[2023A1515012259] ; Zhongshan Municipal Natural Science Foundation, China[200805173640573] ; Zhongshan Municipal Natural Science Foundation, China[210730214049987] ; Zhongshan Municipal Natural Science Foundation, China[221018194369472] ; Project of the Creative Research Group of Zhongshan City, China[CXTD2022011] ; Dazhou Applied Basic Research Foundation, China[23YYJC0002]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001208247200001
出版者HIGHER EDUCATION PRESS
源URL[http://119.78.100.183/handle/2S10ELR8/310959]  
专题中国科学院上海药物研究所
通讯作者Zhao, Guilong; Ti, Huihui
作者单位1.Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
3.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
4.Guangdong Pharmaceut Univ, Sch Chinese Mat Med, Guangzhou 510006, Peoples R China
推荐引用方式
GB/T 7714		 Jiang, Shanshan,Yuan, Jia,Qin, Yanlan,et al. A Concise, Practical Chiral Resolution Approach of Racemic (E)-4,4-Dimethyl-1-(4-nitrophenyl)pent-1-en-3-ol to Its both Enantiomers via Strategy of Diastereomeric Ester Formation and Crystallization Using both N-Boc-D- and N-Boc-L-phenylglycines as Chiral Auxiliaries[J]. CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,2024:10.
APA Jiang, Shanshan.,Yuan, Jia.,Qin, Yanlan.,Luo, Ying.,Jin, Zhengsheng.,...&Ti, Huihui.(2024).A Concise, Practical Chiral Resolution Approach of Racemic (E)-4,4-Dimethyl-1-(4-nitrophenyl)pent-1-en-3-ol to Its both Enantiomers via Strategy of Diastereomeric Ester Formation and Crystallization Using both N-Boc-D- and N-Boc-L-phenylglycines as Chiral Auxiliaries.CHEMICAL RESEARCH IN CHINESE UNIVERSITIES,10.
MLA Jiang, Shanshan,et al."A Concise, Practical Chiral Resolution Approach of Racemic (E)-4,4-Dimethyl-1-(4-nitrophenyl)pent-1-en-3-ol to Its both Enantiomers via Strategy of Diastereomeric Ester Formation and Crystallization Using both N-Boc-D- and N-Boc-L-phenylglycines as Chiral Auxiliaries".CHEMICAL RESEARCH IN CHINESE UNIVERSITIES (2024):10.

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来源：上海药物研究所

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