Fe-BPsalan Complex-Catalyzed Asymmetric [4+2] Cycloaddition of Cyclopentadiene with α,β-Unsaturated Heterocycles

被引:5
|
作者
Chen, Kai-Ge [1 ,2 ]
Lu, Hao [1 ,2 ]
Zhou, Yi-Ming [2 ]
Wan, Xiao-Long [2 ]
Wang, Hao-Yang [2 ]
Xu, Zhen-Jiang [2 ]
Guo, Hai-Ming [1 ]
Che, Chi-Ming [2 ,3 ,4 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Henan, Peoples R China
[2] Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
[3] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Hong Kong, Peoples R China
[4] HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 13期
基金
中国国家自然科学基金;
关键词
DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; DIENOPHILES; REVERSAL; OXIDES; CATION; DIENE;
D O I
10.1021/acs.joc.1c02798
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient iron-catalyzed asymmetric [4 + 2] cycloaddition of cyclopentadiene with alpha,beta-unsaturated acyl imidazoles or 2-cinnamoylisoindoline-1,3-dione derivatives was developed to afford the addition products in high yield and selectivity. Interestingly, the absolute structures of the addition products were controlled by the auxiliaries via different coordination modes with the same type of catalyst.
引用
收藏
页码:8289 / 8302
页数:14
相关论文
共 50 条
  • [41] Trienamine-mediated asymmetric [4+2]-cycloaddition of α, β-unsaturated ester surrogates applying 4-nitro-5-styrylisoxazoles
    Li, Yang
    Lopez-Delgado, Francisco Javier
    Jorgensen, Danny Kaare Bech
    Nielsen, Rune Pagh
    Jiang, Hao
    Jorgensen, Karl Anker
    CHEMICAL COMMUNICATIONS, 2014, 50 (99) : 15689 - 15691
  • [42] Asymmetric [4+2] cycloaddition of cyclopentadiene to N'-tosylimine of N-glyoxyloyl-(2R)-bornane-10,2-sultam
    Bauer, T
    Szymanski, S
    Jezewski, A
    Gluzinski, P
    Jurczak, J
    TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2619 - 2625
  • [43] Kinetics of the [4+2] cycloaddition of cyclopentadiene with (E)-2-aryl-1-cyano-1-nitroethenes
    Radomir Jasiński
    Magdalena Kwiatkowska
    Andrzej Barański
    Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 895 - 899
  • [44] Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4+2] cycloaddition
    Aikawa, Kohsuke
    Akutagawa, Susumu
    Mikami, Koichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12648 - 12649
  • [45] Multiple Activation Catalyst for Asymmetric [4+2] Cycloaddition of Aldehydes with Dienes
    Tomifuji, Rei
    Murano, Shunpei
    Teranishi, Satoru
    Kuroda, Daiki
    Kurahashr, Takuya
    Matsubara, Seijiro
    SYNLETT, 2021, 32 (19) : 1943 - 1947
  • [46] Phthalocyanines and related compounds: XLVI. [4+2]-cycloaddition of tetraazaporphine to dienes of the cyclopentadiene series
    S. V. Dudkin
    E. A. Makarova
    E. A. Luk’yanets
    Russian Journal of General Chemistry, 2008, 78 : 1441 - 1446
  • [47] Divergent Catalysis: Catalytic Asymmetric [4+2] Cycloaddition of Palladium Enolates
    Flesch, Kaylin N.
    Cusumano, Alexander Q.
    Chen, Peng-Jui
    Strong, Christian Santiago
    Sardini, Stephen R.
    Du, Yun E.
    Bartberger, Michael D.
    Goddard, William A., III
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (20) : 11301 - 11310
  • [48] Kinetics of the [4+2] cycloaddition of cyclopentadiene with (E)-2-aryl-1-cyano-1-nitroethenes
    Jasinski, Radomir
    Kwiatkowska, Magdalena
    Baranski, Andrzej
    MONATSHEFTE FUR CHEMIE, 2012, 143 (06): : 895 - 899
  • [49] Phthalocyanines and related compounds: XLVI. [4+2]-cycloaddition of tetraazaporphine to dienes of the cyclopentadiene series
    Dudkin, S. V.
    Makarova, E. A.
    Luk'yanets, E. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (07) : 1441 - 1446
  • [50] Diastereoselective [4+2]cycloaddition of cyclopentadiene to N-tosyliminoacetyl derivatives of chiral secondary alcohols
    Szymanski, S
    Marzec, M
    Jurczak, J
    POLISH JOURNAL OF CHEMISTRY, 2002, 76 (06) : 831 - 837