An Unexpected N-Heterocyclic Carbene-Catalyzed Annulation of Enals and Nitroso Compounds

被引：60
|
作者：
Yang, Limin [1 ]
Tan, Bin [1 ]
Wang, Fei [1 ]
Zhong, Guofu [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期
关键词：
INTRAMOLECULAR STETTER REACTION; GAMMA-BUTYROLACTONES; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC CARBENES; BENZOIN CONDENSATION; CONJUGATE UMPOLUNG; CARBONYL-COMPOUNDS; STABLE CARBENES; METAL-COMPLEXES;
D O I：
10.1021/jo802515g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The N-heterocyclic carbene (NHC)-catalyzed annulation of enals with nitroso compounds in the presence of DBU in THF has been described. Unexpected seven-membered 4-azalactones were formed according to a process involving a 1,2-Bamberger-type rearrangement.
引用
收藏
页码：1744 / 1746
页数：3
相关论文
共 50 条
  • [41] Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates
    Zhao, Liang-Liang
    Li, Xing-Shuo
    Cao, Li-Li
    Zhang, Rui
    Shi, Xiao-Qian
    Qi, Jing
    CHEMICAL COMMUNICATIONS, 2017, 53 (44) : 5985 - 5988
  • [42] N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN
    Fan, Ye-Cheng
    Du, Guang-Fen
    Sun, Wan-Fu
    Kang, Wei
    He, Lin
    TETRAHEDRON LETTERS, 2012, 53 (17) : 2231 - 2233
  • [43] N-Heterocyclic Carbene-Catalyzed β-Indolylation of α-Bromoenals with Indoles
    Sun, Shaofa
    Lang, Ming
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (24) : 5704 - 5708
  • [44] Enantioselective N-heterocyclic carbene-catalyzed synthesis of indenopyrones
    Chen, Kun-Quan
    Zhang, Han-Ming
    Wang, Dong-Ling
    Sun, De-Qun
    Ye, Song
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6694 - 6697
  • [45] N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
    Gelat, Fabien
    Patra, Atanu
    Pannecoucke, Xavier
    Biju, Akkattu T.
    Poisson, Thomas
    Besset, Tatiana
    ORGANIC LETTERS, 2018, 20 (13) : 3897 - 3901
  • [46] Palladium N-Heterocyclic Carbene-Catalyzed Aminations: An Outline
    Umabharathi, S. B.
    Neetha, Mohan
    Anilkumar, Gopinathan
    TOPICS IN CURRENT CHEMISTRY, 2024, 382 (01)
  • [47] N-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols
    Phillips, Eric M.
    Riedrich, Matthias
    Scheidt, Karl A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13179 - 13181
  • [48] N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides
    Xia Dengpeng
    Luo Jinvun
    He Lin
    Cai Zhihua
    Du Guangfen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 622 - 630
  • [49] N-heterocyclic carbene-catalyzed arene formation reactions
    Tingting Li
    Zhichao Jin
    Yonggui Robin Chi
    Science China(Chemistry), 2022, 65 (02) : 210 - 223
  • [50] Enantioselective N-Heterocyclic Carbene-Catalyzed Synthesis of Trifluoromethyldihydropyridinones
    Wang, Dong-Ling
    Liang, Zhi-Qin
    Chen, Kun-Quan
    Sun, De-Qun
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11): : 5900 - 5905
12345