Nickel-Catalyzed Enantioselective Reductive Spirocyclization of 1,6-Enynes with o -Bromobenzaldehydes

被引：0
|
作者：
Guo, Haoyun [1 ]
Chen, Yate [2 ]
Kong, Wangqing [1 ]
机构：
[1] Wuhan Univ, Inst Adv Studies IAS, Wuhan 430072, Peoples R China
[2] Huazhong Agr Univ, Coll Chem, Wuhan 430070, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2025年 / 57卷 / 08期
基金：
中国国家自然科学基金;
关键词：
nickel catalysis; enantioselectivity; reductive spirocyclization; 1,6-enynes; spiroindanones; COUPLING REACTIONS; SPIRO COMPOUNDS; CYCLIZATION; HALIDES; NOMENCLATURE;
D O I：
10.1055/a-2456-9530
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We developed a Ni-catalyzed asymmetric reductive spirocyclization of 1,6-enynes with o-haloaryl aldehydes. This approach provides an efficient method for the construction of chiral spiroindanone pyrrolidine derivatives in good yields with excellent enantio- and diastereoselectivity (up to 99% ee, >20:1 dr). This reaction does not require pre-prepared organometallic reagents and exhibits excellent substrate compatibility.
引用
收藏
页码：1448 / 1456
页数：9
相关论文
共 50 条
  • [21] Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron
    Hsieh, Jen-Chieh
    Hong, Ya-Chun
    Yang, Chun-Ming
    Mannathan, Subramaniyan
    Cheng, Chien-Hong
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1615 - 1619
  • [22] Co-Catalyzed Reductive Cyclization of Acrylate-Containing 1,6-Enynes
    Yang, Zhantao
    Hou, Shenyin
    Cheng, Yunfan
    Sun, Li
    Yang, Chun-Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2022, : 13339 - 13345
  • [23] Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes
    Corkey, Britton K.
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) : 2764 - +
  • [24] Enantioselective Cycloisomerization of 1,6-Enynes Catalyzed by Chiral Diphosphane- Palladium Complexes
    Dept. of Synth. Chem./Biol. Chem., Faculty of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-01, Japan
    不详
    Angew Chem (Int Ed Engl), 6 (662-663):
  • [25] Enantioselective IrI-Catalyzed Carbocyclization of 1,6-Enynes by the Chiral Counterion Strategy
    Barbazanges, Marion
    Auge, Mylene
    Moussa, Jamal
    Amouri, Hani
    Aubert, Corinne
    Desmarets, Christophe
    Fensterbank, Louis
    Gandon, Vincent
    Malacria, Max
    Ollivier, Cyril
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (49) : 13789 - 13794
  • [26] Enantioselective cycloisomerization of 1,6-enynes catalyzed by chiral diphosphane-palladium complexes
    Goeke, A
    Sawamura, M
    Kuwano, R
    Ito, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06): : 662 - 663
  • [27] Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ-Butyrolactam
    Zhang, Liren
    Wang, Yuanfang
    Tang, Junlong
    Wu, Wanqing
    Jiang, Huanfeng
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01): : 894 - 898
  • [28] Enantioselective Platinum-Catalyzed Tandem Hydroarylation-Cycloisomerization of 1,6-Enynes
    Toullec, Patrick Yves
    Chao, Chung-Meng
    Chen, Qian
    Gladiali, Serafino
    Genet, Jean-Pierre
    Michelet, Veronique
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2401 - 2408
  • [29] Rhodium(I)-Catalyzed Cycloisomerization of 1,6-Enynes
    Matsushima, Yuji
    Phillips, Eric M.
    Bergman, Robert G.
    Ellman, Jonathan A.
    SYNLETT, 2015, 26 (11) : 1533 - 1536
  • [30] Palladium-Catalyzed Cyclization of 1,6-Enynes
    Liu Wenjuan
    Chen Pinhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2077 - 2091
12345