Citation: Yao Zhong Jiang, Xiao Ming Feng, Liu Zhu Gong, Zhi Li, Gui Su Yang, Ai Qiao Mi. ASYMMETRIC SYNTHESIS XXⅧ:ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES CATALYZED BY NEW CHIRAL CATALYST-(4R,8R,9S)-CAMPHANE[8,9-b]-1,3,2-OXATHIOBOROLIDINE[J]. Chinese Chemical Letters, ;1996, 7(5): 415-418. shu

ASYMMETRIC SYNTHESIS XXⅧ:ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES CATALYZED BY NEW CHIRAL CATALYST-(4R,8R,9S)-CAMPHANE[8,9-b]-1,3,2-OXATHIOBOROLIDINE

Union Laboratory of Asymmetric Synthesis,Chengdu Institute of Organic Chemistry. Chinese Academy of Sciences, Chengdu 610041

Received Date: 13 October 1995

(4R,8R,9S)-Camphane[8,9-b]-1,3,2-oxathioborolidine prepared from (1R,2S,3R)-3-mercapto-camphol with borane was used as catalyst in the enantioselective reduction of aromatic ketones:moderate enantioselectivities with e.e.7.44%-51.04% have been obtained for aromatic ketones with 20% mol catalyst,73.78% e.e for ω-bromo acetophenone with 100% mol catalyst.
1. [1]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
2. [2]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
3. [3]
  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
4. [4]
  Weiping Guo , Ying Zhu , Hong-Hua Cui , Lingyun Li , Yan Yu , Zhong-Zhen Luo , Zhigang Zou . β-Pb₃P₂S₈: A new optical crystal with exceptional birefringence effect. Chinese Chemical Letters, 2025, 36(2): 110256-. doi: 10.1016/j.cclet.2024.110256
5. [5]
  Xiaohan Wang , Xue Guo , Zhuo Song , Chen Guan , Chengyu Yang , Tianyang Li , Yukun Zhu , Yan Xu . Interface engineering of Co9S8/Ni3S2 heterojunction with robust stability for boosting peroxymonosulfate activation. Chinese Journal of Structural Chemistry, 2026, 45(2): 100771-100771. doi: 10.1016/j.cjsc.2025.100771
6. [6]
  Yun Wang , Huage Lin , Jiaxiang Zong , Mengjiao Yu , Guangyu Wu , Weinan Xing . Interface design of S-scheme Co9S8/flower-like g-C3N4 van der Waals heterojunction with enhanced photocatalytic hydrogen production and tetracycline hydrochloride degradation. Chinese Journal of Structural Chemistry, 2026, 45(2): 100798-100798. doi: 10.1016/j.cjsc.2025.100798
7. [7]
  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
8. [8]
  Hao GUO , Tong WEI , Qingqing SHEN , Anqi HONG , Zeting DENG , Zheng FANG , Jichao SHI , Renhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co₉S₈/Ni₃S₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085
9. [9]
  Feng Wu , Yuanjiu Xiao , Mengran Wei , Guoqiang Wang , Jian-Jun Feng . Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes. Chinese Chemical Letters, 2026, 37(3): 111963-. doi: 10.1016/j.cclet.2025.111963
10. [10]
  Hongshan Wang , Zhenglong Li , Ran An , Zhenyou Wang , Juanjuan Lu , Guansong Zheng , Zhihua Yang , Yu Chu , Junjie Li . NaAg3Ga8S14: A new diamond-like framework infrared nonlinear optical material derived from AgGaS2. Chinese Journal of Structural Chemistry, 2025, 44(12): 100757-100757. doi: 10.1016/j.cjsc.2025.100757
11. [11]
  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
12. [12]
  Long Yin , Yuxin Shi , Rong Meng , Jiapei Shan , Weiwei Sun , Weijun Yao , Xiaowei Dou , Dong Guo . Development and enantioselective synthesis of spirobiindoles via Rh-catalyzed asymmetric arylation-spirocyclization sequence. Chinese Chemical Letters, 2026, 37(3): 111258-. doi: 10.1016/j.cclet.2025.111258
13. [13]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
14. [14]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
15. [15]
  Qi Sun , Hongshan Wang , Linlin Liu , Zuxin Chen , Junjie Li , Shilie Pan . A new selenide semiconductor NaMn₃Ga₃Se₈ with strong second-harmonic generation and significant luminescence property. Chinese Journal of Structural Chemistry, 2025, 44(6): 100591-100591. doi: 10.1016/j.cjsc.2025.100591
16. [16]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
17. [17]
  Xiuhua Wang , Jianrong Steve Zhou . A dicationic nickel complex-catalyzed asymmetric synthesis of chiral benzylic amines: Evolution from reductive amination to borrowing hydrogen reaction. Chinese Chemical Letters, 2026, 37(2): 111148-. doi: 10.1016/j.cclet.2025.111148
18. [18]
  Zhen-Qi Wang , Lin-Wen Wei , Zhao-Qing Wang , Yan-Jie Yang , Yu Zhao , Song Liu , Yuan Huang . Modular synthesis of polyfunctionalized axial-chiral 2-arylpyridines via cobalt-catalyzed asymmetric [2 + 2 + 2] cycloaddition of diynes and nitriles. Chinese Chemical Letters, 2026, 37(4): 111377-. doi: 10.1016/j.cclet.2025.111377
19. [19]
  Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
20. [20]
  Weilong Liu , Jipeng Dong , Luyao Zhang , Ning Li , Yangqin Gao , Lei Ge . Dynamic tuning of d-p orbital hybridization during sulfur vacancy evolution in Co9S8 toward efficient overall water splitting. Chinese Journal of Structural Chemistry, 2025, 44(9): 100661-100661. doi: 10.1016/j.cjsc.2025.100661

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1676)
HTML views(29)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return