Full-Text Search:
Home|Journal Papers|About CNKI|User Service|FAQ|Contact Us|中文
《CHEMICAL RESEARCH IN CHINESE UNIVERSITIES》 1999-09
Add to Favorite Get Latest Update

Synthesis of 3-Bicyclo[3.3.0]octene Derivatives Containing Multiple Chiral Centers

HUANG Hui; CHEN Qing-Hua(Department of Chemistry, Betjing Normal University, Beijing 100875, China)  
The tandem asymmetric Michael addition/intramolecular nucleophilic substitution of the novel chiral source, 3-bromo-5- (1-menthyloxy)-2 (5H)-furanone (1) with some carbon nucleophiles has been investigated. The asymmetric reaction can yield optically pure 3-bicyclo [3.3.0]octene derivatives containing two novel stereogenic chiral centers. The chemical structure and configuration of these 3-bicyclo[3.3.0]octene compounds were identified on the basis of their elemental analytical data and spectroscopic data, such as[α] , UV, IR,1H NMR, 13C NMR, MS and X-ray crystallography.This asymmetric reaction can provide an important strategy in synthesis of some optically pure 3-bicyclo[3. 3. 0]octene compounds and some biologically active molecules.
【Fund】: 国家自然科学基金!29672004
【CateGory Index】: O621
Download(CAJ format) Download(PDF format)
CAJViewer7.0 supports all the CNKI file formats; AdobeReader only supports the PDF format.
【References】
Chinese Journal Full-text Database 10 Hits
1 Feng ShujuanZhang GuanxinQi Chuanmin (Department of Chemistry, Beijing Normal University, 100875, Beijing, C hina);SYNTHESIS OF NOVEL CHIRAL CONDENSED RING LACTONES[J];Journal of Beijing Normal University(Natural Science);2003-01
2 LI Xue Qiang, CHEN Qinq Hua  (Department of Chemistry, Beijing Normal University, Beijing 100875, China);Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives[J];Chemical Research In Chinese Universities;2001-10
3 JIAN Tian-Ying, WANG Zhao-Yang, WANG Jian-Ping, CHEN Qing-Hua(Department of Chemistry, Beijing Normal Universiry, Beijing 100875, China;Department of Chemistry, South China Normal University, Guangzhou 510631, China;Department of Chemistry, Luoyang Teache;A Novel Synthesis Method of 1-Aza-2,8-dioxabicyclo[3.3.0] octane Derivatives[J];Chemical Research In Chinese Universities;2002-04
4 FU Yu Qin 1, ZHANG Xi Yun 2, CHEN Qing Hua 1,2* (1. Department of Chemistry, Luoyang Normal College, Luoyang 471022, China; 2. Department of Chemistry, Beijing Normal University, Beijing 100875, China);Structure Characterization and Resolution of Spiro cyclopropane Compounds Containing Multiple Chiral Centers[J];Chemical Research In Chinese Universities;2003-04
5 HUANG Hai-Hong 1*, ZHANG Xiang 1, LIN Zi-Yun 1, CHEN Qing-Hua 2 (1. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China; 2. Department of Chemistry, Beijing Normal University, Beijing 100875, China);Synthesis of Chiral 5-l-Menthyloxy-butyrolacto [3,4-d]isoxazoline Derivatives[J];Chemical Research In Chinese Universities;2003-11
6 YU Zhao-Lian, LI Sen-Lan, GUO Jin-Bo, CHEN Qing-Hua~* (Department of Chemistry, Luoyang Normal College, Luoyang 470022, China);An Efficient Approach to the Synthesis of Spiro-cyclopropane Derivatives Utilizing 4-Methoxy-2-bromobutyrolactone[J];Chemical Research In Chinese Universities;2005-05
7 HE Lan, ZHANG Wei, LIU Yu-Mei, LI Ming, CHEN Qing-Hua * (Department of Chemistry, Beijing Normal University, Beijing 100875, China);Syntheses and Structures of Some Functionalized Optically Active Butanediol Derivatives[J];Chemical Journal of Chinese Universities;2006-03
8 ZHENG Lü-yin,YANG Ding-qiao,WANG Zhao-yang,Li Wen-hui,JIANG Qi-jun(College of Chemistry and Environment,South China Normal University,Guangzhou 510631,China);Application of 5-Alkoxy-2(5H)-furanone in Organic Synthesis[J];Chinese Journal of Synthetic Chemistry;2005-05
9 ZHU Hong,MA Yin-jian,LI Xue-qiang(a.Key Laboratory of Energy Sources and Chemical Engineering;b.Development Center of Natural Products and Medication;c.Department of Chemistry and Chemical Engineering,1.Ningxia University,Yinchuan 750021,China);Synthesis of Chiral Multicarbonyl Compounds[J];Chinese Journal of Synthetic Chemistry;2007-03
10 Zhang Xiang, Lin Ziyun, Chen Qinghua#,Huang Haihong* (Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050; #Department of Chemistry, Beijing Normal University, Beijing 100875, China);The Total Synthesis of goodyeroside A[J];Chemistry;2004-05
【Citations】
Chinese Journal Full-text Database 2 Hits
1 Chen, Qing-Hua~* Geng, Zhe (Department of Chemistry, Beijing Normal University, Beijing, 100875);A New Chiral Source Optically Pure 5-(1-MenthyIoxy-3, 4-dichloro-2 (5H) -furanone, Its Synthesis and Structure[J];Acta Chimica Sinica;1993-06
2 CHEN Qing-Hua, ZOU Chang (Department of Chemistry, Beijing Normal University, 100875 Beijing);Industrial Synthesis of Optically Active Compounds[J];Chinese Journal of Organic Chemistry;1994-01
【Co-citations】
Chinese Journal Full-text Database 10 Hits
1 Huang Min Chen Qinghua (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);STUDIES ON TANDEM ASYMMETRIC DOUBLE MICHAEL ADDTION AND INTERNAL NUCLEOPHILIC SUBSTITUTION[J];JOURNAL OF BEIJING NORMAL UNIVERSITY(NATURAL SCIENCE);2000-01
2 Cui Jialing Chen Qingde Du Baoshan Li He (Department of Chemistry, Beijing Normal University, 100875, Binjing, China);ASYMMETRIC MICHAEL ADDITION OF CHIRAL 5[(1S)-ENDO-BORNYLOXY]-2(5H)-FURANONE WITH THIOPHENOLS[J];JOURNAL OF BEIJING NORMAL UNIVERSITY(NATURAL SCIENCE);2000-02
3 Qi Chuanmin Guo Xuefeng Zhang Guanxin Feng Shujuan Yang Lingchun (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);SYNTHESIS AND ACTIVITIES OF NOVEL CHIRAL AMINODIOL CATALYSTS[J];Journal of Beijing Normal University(Natural Science);2001-05
4 Qi Chuanmin Fu Limin Wang Liyuan He Yihui Xu Ying (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);SYNTHESIS OF NOVEL CHIRAL LACTONE SUBSTITUTED 2-AMINO-THIADIAZOLE[J];Journal of Beijing Normal University(Natural Science);2002-03
5 ZOU Chang 1, DU Bao shan 2, CHEN Qing hua 2 (1.Nanchang University,Nanchang 330027,China;2.Beijing Normal University,Beijing 100875,China);Asymmetric Michael Addition Reaction of Chiral 5-(l-menthyloxy)-2(5H)-furanone[J];JOURNAL OF JIANGXI NORMAL UNIVERSITY (NATURAL SCIENCES EDITION);1999-03
6 ZOU Chang1, DU Bao shan2, CHEN Qing hua2 (1.Shunde Polytechnic,Shunde Guangdong 528300,China;2.Beijing Normal University,Beijing 100875,China);Asymmetric 1,3-Dipolar Cycloaddition of Chiral 5-(l-menthyloxy)-2(5H)-furanone[J];Journal of Jiangxi Normal University (Natural Sciences Edition);2001-01
7 GE Jun-ying~1,ZHOU Guo-bin~2,LIU Fang~1,SONG Xin-lu~1,LUO Guo-qiang~1,CHEN Hui-zong~(1*)(1.Institute of Chemistry and Chemical Engineering Sciences,Jiangxi Normal University,Nanchang 330027,China;2.College of Chemistry and Environmental Engineering,Shandong Univeristy of Science and Technology,Qindao Shandong 266510,China);Natural Chiron Borneol Applied in α-Substitution Lactic Acid Asymmetric Synthesis[J];Journal of Jiangxi Normal University(Natural Sciences Edition);2006-05
8 LI Xue-Qiang~, GONG Bo-Lin, WANG Feng-Rong (Department of Chemistry & Chemical Engineering, Ningxia University, Yinchuan 750021, China) CHEN Qing-Hua, WANG Zhi-Dan (Department of Chemistry, Beijing Normal University, Beijing 100875, China);Michael Addition-elimination Reactions of Chiral 5-Alkoxy-3,4-dihalo-2(5H)-Furanones in DMF[J];Chemical Research In Chinese Universities;2001-01
9 HU Ai Guo 1, WANG Shan Wei 2, HAN Jun 1, WANG Ji Tao 1  (1. Department of Chemistry, State Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China; 2. Central Laboratory, Nankai University, Tia;Asymmetric Synthesis of α-Amino Acids[J];Chemical Research In Chinese Universities;2001-03
10 GE Jun-ying(Key Laboratory of Applied Chemistry and Chemical Biology in Jiangxi Province,Yichun University,Yichun 336000,Jiangxi,China);A Synthetic Method of S-(+)Lactic Acid with High Optical Purity and Production Ratio[J];Hubei Agricultural Sciences;2011-08
China Proceedings of conference Full-text Database 1 Hits
1 Fu Yong-ju Wang Jian-ping Liu Song-qing Cao Lan-lan Chen Qing-hua ( Department of Chemistry, Luoyang Normal University, Luoyang 471022) ( Chemical Engineering & Pharmaceutis College, Henan University of Science and Technology, Luoyang 471003);Synthesis and Structure of Chiral -4-Double Butenolide Ether[A];[C];2006
【Co-references】
Chinese Journal Full-text Database 10 Hits
1 Huang Min Chen Qinghua (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);STUDIES ON TANDEM ASYMMETRIC DOUBLE MICHAEL ADDTION AND INTERNAL NUCLEOPHILIC SUBSTITUTION[J];JOURNAL OF BEIJING NORMAL UNIVERSITY(NATURAL SCIENCE);2000-01
2 Cui Jialing Chen Qingde Du Baoshan Li He (Department of Chemistry, Beijing Normal University, 100875, Binjing, China);ASYMMETRIC MICHAEL ADDITION OF CHIRAL 5[(1S)-ENDO-BORNYLOXY]-2(5H)-FURANONE WITH THIOPHENOLS[J];JOURNAL OF BEIJING NORMAL UNIVERSITY(NATURAL SCIENCE);2000-02
3 Qi Chuanmin Guo Xuefeng Zhang Guanxin Feng Shujuan Yang Lingchun (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);SYNTHESIS AND ACTIVITIES OF NOVEL CHIRAL AMINODIOL CATALYSTS[J];Journal of Beijing Normal University(Natural Science);2001-05
4 Qi Chuanmin Fu Limin Wang Liyuan He Yihui Xu Ying (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);SYNTHESIS OF NOVEL CHIRAL LACTONE SUBSTITUTED 2-AMINO-THIADIAZOLE[J];Journal of Beijing Normal University(Natural Science);2002-03
5 Huang Xiaobin Qi Chuanmin Fu Limin (Department of Chemistry, Beijing Normal University, 100875, Beijing, China);THE ASYMMETRIC MICHAEL ADDITION REACTION OF A NEW TYPE OF CHIRAL FURANONE[J];Journal of Beijing Normal University(Natural Science);2002-05
6 Feng ShujuanZhang GuanxinQi Chuanmin (Department of Chemistry, Beijing Normal University, 100875, Beijing, C hina);SYNTHESIS OF NOVEL CHIRAL CONDENSED RING LACTONES[J];Journal of Beijing Normal University(Natural Science);2003-01
7 ZOU Chang 1, DU Bao shan 2, CHEN Qing hua 2 (1.Nanchang University,Nanchang 330027,China;2.Beijing Normal University,Beijing 100875,China);Asymmetric Michael Addition Reaction of Chiral 5-(l-menthyloxy)-2(5H)-furanone[J];JOURNAL OF JIANGXI NORMAL UNIVERSITY (NATURAL SCIENCES EDITION);1999-03
8 ZOU Chang1, DU Bao shan2, CHEN Qing hua2 (1.Shunde Polytechnic,Shunde Guangdong 528300,China;2.Beijing Normal University,Beijing 100875,China);Asymmetric 1,3-Dipolar Cycloaddition of Chiral 5-(l-menthyloxy)-2(5H)-furanone[J];Journal of Jiangxi Normal University (Natural Sciences Edition);2001-01
9 Zhao Yang WANG;Tian Ying JIAN; Qing Hua CHEN(Department of Chemistry,Beijing Normal University, Beijing 100875);Asymmetric Photocatalyzed Addition of Cyclic Ammes to the Chiral 5-(l)-Menthyloxy-2(5H)-furanone[J];中国化学快报(英文版);1999-11
10 Zhao Yang WANG2, Jia Ling CUI3, Bao Shan DU1*, Qing Hua CHEN1 1Department of Chemistry, Beijing Normal University, Beijing 100875 2Present address: Dept. of Chem., South China Nor. Univ, Guangzhou 510631 3Present address: School of Pharm., Beijing Univ,;Studies on New Additions to 5-Methoxy-2 (5H)-Furanone: 1, 4-Addition of Grignard Reagents, and 1,3-Dipolar Cycloaddition of Silyl Nitronates[J];中国化学快报(英文版);2001-04
【Secondary References】
Chinese Journal Full-text Database 10 Hits
1 PEI Qiang1,2) HOU Jing1) LI Shuxian3) LI Jueyu1) HE Li1) Li Huamin1)(1)College of Chemistry,Beijing Normal University,100875,Beijing,China;2)College of Chemistry,Xinyang Normal University,464000,Xinyang,Henan,China;3)Department of Chemistry,Handan College,056005,Handan,Hebei,China);THE RESEARCH OF THE REGIOSELECTIVE RING OPENING REACTION OF A NEW TYPE ENANTIOPURE BICYCLIC FUSED AZIRIDINES[J];Journal of Beijing Normal University(Natural Science);2008-01
2 LIU Fang,GE Jun-ying,LUO Guo-qiang,SONG Xin-lu,WANG Qi,CHEN Hui-zong(Institute of Chemistry and Chemical Engineering Sciences,Jiangxi Normal University,Nanchang 330027,China);The Asymmetric Diels-Alder Reaction of Cycolpentadiene with Bornyl Acrylate[J];Journal of Jiangxi Normal University(Natural Sciences Edition);2006-04
3 HUANG Hai-Hong 1*, ZHANG Xiang 1, LIN Zi-Yun 1, CHEN Qing-Hua 2 (1. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China; 2. Department of Chemistry, Beijing Normal University, Beijing 100875, China);Synthesis of Chiral 5-l-Menthyloxy-butyrolacto [3,4-d]isoxazoline Derivatives[J];Chemical Research In Chinese Universities;2003-11
4 YU Zhao-Lian, LI Sen-Lan, GUO Jin-Bo, CHEN Qing-Hua~* (Department of Chemistry, Luoyang Normal College, Luoyang 470022, China);An Efficient Approach to the Synthesis of Spiro-cyclopropane Derivatives Utilizing 4-Methoxy-2-bromobutyrolactone[J];Chemical Research In Chinese Universities;2005-05
5 ZHENG Lü-yin,YANG Ding-qiao,WANG Zhao-yang,Li Wen-hui,JIANG Qi-jun(College of Chemistry and Environment,South China Normal University,Guangzhou 510631,China);Application of 5-Alkoxy-2(5H)-furanone in Organic Synthesis[J];Chinese Journal of Synthetic Chemistry;2005-05
6 SONG Xiumei,WANG Zhaoyang,FU Jianhua,LI Jianxiao(School of Chemistry and Environment,South China Normal University,Guangzhou 510631,China);THE TANDEM MICHAEL ADDITION-ELIMINATION REACTION OF 5-ALKOXY-3,4-DIHALO-2(5H)-FURANONE WITH SOLVENT DMF AND ITS REACTION MECHANISM[J];Journal of South China Normal University(Natural Science Edition);2009-04
7 Zhang Xiang, Lin Ziyun, Chen Qinghua#,Huang Haihong* (Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050; #Department of Chemistry, Beijing Normal University, Beijing 100875, China);The Total Synthesis of goodyeroside A[J];Chemistry;2004-05
8 GUO, Jin-Boa ZHANG, Xi-Yunb CHEN, Qing-Hua*,a,b (a Department of Chemistry, Luoyang Normal College, Luoyang 471022) (b Department of Chemistry, Beijing Normal University, Beijing 100875);Study of the Synthetic Method of Cyclopropane Derivatives Based on 3-Bromo-2,5-dihydro-5-menthyloxyfuran-2-one:Asymmetric Tandem Reaction Starting by Carbon Nucleophile[J];Acta Chimica Sinica;2006-19
9 Li,Jianxiao Xue,Fuling Tan,Yuehe Luo,Shihe Wang,Zhaoyang(School of Chemistry and Environment,South China Normal University,Guangzhou 510006);Sonogashira Coupling Reaction of 5-Substituted 3,4-Dihalo-2(5H)-furanones[J];Acta Chimica Sinica;2011-14
10 Li,Jianxiao Wang,Zhaoyang Xue,Fuling Luo,Shihe(School of Chemistry and Environment,South China Normal University,Guangzhou 510006);Synthesis of Novel Tricyclic Fused 2(5H)-Furanone Derivatives with 1,2,3-Triazole Structure[J];Acta Chimica Sinica;2011-23
【Secondary Citations】
Chinese Journal Full-text Database 1 Hits
1 Chen, Qing-Hua~* Geng, Zhe (Department of Chemistry, Beijing Normal University, Beijing, 100875);A New Chiral Source Optically Pure 5-(1-MenthyIoxy-3, 4-dichloro-2 (5H) -furanone, Its Synthesis and Structure[J];Acta Chimica Sinica;1993-06
©2006 Tsinghua Tongfang Knowledge Network Technology Co., Ltd.(Beijing)(TTKN) All rights reserved