Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

Chemical Research in Chinese Universities ›› 1999, Vol. 15 ›› Issue (1): 23-28.

• Articles • Previous Articles Next Articles

Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang

Department of Chemistry, Hubei University, Wuhan, 430062

Received:1998-04-20 Online:1999-01-24 Published:2011-08-17
Supported by:
Supported by the National Natural Science Foundation of China.

Abstract

Abstract: (+)-Camphor derived N-crotonoylsultam 2, readily available from chiral auxiliary bornane-10,2-sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n-butyl, n-pentyl, n-hexyl, n-heptyl) under the control of CuI or not being at low temperatures, giving diasteroisomers 4, 5 respectively. After nondestructive cleavage both enantiomers of the acid and alcohol were obtained in high e. e.%. The d. e.% of 4,5 was determined by HPLC, and the assignment of these values was discussed by analyzing ¹H NMR(500 MHz).

Key words: Bornanesultam, N-Crotonoly sultam, Michael addition, Synthesis

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang . Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam[J]. Chemical Research in Chinese Universities, 1999, 15(1): 23-28.

[1]	FAN Kui, SUN Yining, XU Pengcheng, GUO Jian, LI Zhenhua, SHAO Mingfei. Single-atom Catalysts Based on Layered Double Hydroxides [J]. Chemical Research in Chinese Universities, 2022, 38(5): 1185-1196.
[2]	YANG Shengqing, ZHAO Jinnan, CHEN Shuo, ZHAO Jingbo. Flexible Self-healing Cross-linked Polyamides Synthesized Through Bulk Michael Addition, Polycondensation, and Diels-Alder Reaction [J]. Chemical Research in Chinese Universities, 2022, 38(4): 968-973.
[3]	JI Yuancheng, XU Jiayun, SUN Hongcheng, and LIU Junqiu. Artificial Photosynthesis(AP): from Molecular Catalysts to Heterogeneous Materials [J]. Chemical Research in Chinese Universities, 2022, 38(3): 688-697.
[4]	CHEN Juan, WANG Jiajia, CHEN Chongan and YANG Guoyu. Two New Borates Built by Different Types of {B₉} Cluster Units [J]. Chemical Research in Chinese Universities, 2022, 38(3): 744-749.
[5]	Mohammad Javad TAGHIZADEH, Maryam Saleh MOHAMMADNIA, Masoumeh GHALKHANI, Esmail SOHOULI. Improved Method for the Total Synthesis of Azaperone and Investigation of Its Electrochemical Behavior in Aqueous Solution [J]. Chemical Research in Chinese Universities, 2022, 38(2): 546-551.
[6]	SUN Xiao-Shuang, QIN Dan, LI Xu-Yan, YANG Guo-Yu. A New Tubular Borate Built by[B₁₄O₂₄(OH) ₆]^12- Cluster Units [J]. Chemical Research in Chinese Universities, 2022, 38(1): 123-127.
[7]	WANG Zelin, LIU Guihao, SHEN Tianyang, TAN Ling, ZHAO Yufei, SONG Yu-Fei. Remote Synthesis of Layered Double Hydroxide Nanosheets Through the Automatic Chemical Robot [J]. Chemical Research in Chinese Universities, 2022, 38(1): 217-222.
[8]	ZHANG Xiaosi, YANG Miao, TIAN Peng, LIU Zhongmin. Progress in Seed-assisted Synthesis of (Silico) Aluminophosphate Molecular Sieves [J]. Chemical Research in Chinese Universities, 2022, 38(1): 1-8.
[9]	LUAN Huimin, WU Qinming, ZHANG Jian, WANG Yeqing, MENG Xiangju, XIAO Feng-Shou. Sustainable Synthesis of Core-Shell Structured ZSM-5@Silicalite-1 Zeolite [J]. Chemical Research in Chinese Universities, 2022, 38(1): 136-140.
[10]	FANG Yuan, HEYDARI Zahra, LIU Chenghao, ZHANG Nianyue, CUCCIA Louis A., IVASENKO Oleksandr, PEREPICHKA Dmitrii F.. Glaser Coupling of Substituted Anthracene Diynes on a Non-metallic Surface at the Vapor-Solid Interface [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1143-1148.
[11]	ZHAO Lei, YANG Ge, GUO Hailing, WANG Chunzheng, WANG Lijuan, Svetlana MINTOVA. Effect of Sodium Concentration on the Synthesis of Faujasite by Two-step Synthesis Procedure [J]. Chemical Research in Chinese Universities, 2021, 37(5): 1137-1142.
[12]	ZHANG Ling, FU Yihong, DING Yue, MENG Jiao, WANG Zhenchao, WANG Peiyi. Antibacterial Activity of Novel 18β-Glycyrrhetinic Hydrazide or Amide Derivatives [J]. Chemical Research in Chinese Universities, 2021, 37(3): 662-667.
[13]	DONG Xin, CHEN Xi, ZHOU Zhaohui. Efficient Synthesis of p-Hydroxyphenyl Ethanol from Hydrogenation of Methyl p-Hydroxyphenylacetate with CNTs-promoted Cu-Zr Catalyst [J]. Chemical Research in Chinese Universities, 2021, 37(3): 745-750.
[14]	LI Yuan, LI Ruizhe, LI Zhenhua, WEI Weiqin, OUYANG Shuxin, YUAN Hong, ZHANG Tierui. Effect of Support on Catalytic Performance of Photothermal Fischer-Tropsch Synthesis to Produce Lower Olefins over Fe₅C₂-based Catalysts [J]. Chemical Research in Chinese Universities, 2020, 36(6): 1006-1012.
[15]	ZHANG Baochang, LI Yulei, SHI Weiwei, WANG Tongyue, ZHANG Feng, LIU Lei. Chemical Synthesis of Proteins Containing 300 Amino Acids [J]. Chemical Research in Chinese Universities, 2020, 36(5): 733-747.

Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments