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

页码：8289 / 8302

页数：14

共 50 条

[21] [4+2] dimerization and cycloaddition reactions of α,β-unsaturated selenoaldehydes and selenoketones
Li, GM
Niu, SQ
Segi, M
Zingaro, RA
Yamamoto, H
Watanabe, K
Nakajima, T
Hall, MB
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1565 - 1575
[22] Asymmetric N-Heterocyclic Carbene-catalyzed [4+2] Cycloaddition of Ketenes with α-cyanochalcones
Sun Lihui
Liang Zhiqin
Ye Song
ACTA CHIMICA SINICA, 2014, 72 (07) : 841 - 844
[23] Synthesis of optically active dihydropyrans from asymmetric [4+2] cycloaddition of β,γ-unsaturated α-ketoesters with allenic esters
Pei, Cheng-Kui
Jiang, Yu
Shi, Min
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (22) : 4355 - 4361
[24] Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base
Terada, Masahiro
Nii, Hiroyuki
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) : 1760 - 1763
[25] Phosphine-catalyzed [4+2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones
Yang, Wenjun
Zhang, Yunpeng
Qiu, Shuxian
Zhao, Chuanqi
Zhang, Lei
Liu, Honglei
Zhou, Leijie
Xiao, Yumei
Guo, Hongchao
RSC ADVANCES, 2015, 5 (77): : 62343 - 62347
[26] Copper-Catalyzed Stereoselective [4+2] Cycloaddition of β,γ-Unsaturated α-Keto Esters and 2-Vinylpyrroles in Water
Zhao, Shuangshuang
Li, Kuiliang
Sun, Xiang
Zha, Zhenggen
Wang, Zhiyong
ORGANIC LETTERS, 2022, 24 (23) : 4224 - 4228
[27] Enantioselective rhodium-catalyzed [4+2] cycloaddition of alpha, beta-unsaturated imines and isocyanates
Oberg, Kevin M.
Rovis, Tomislav
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[28] Enantioselective [4+2] cycloaddition reaction of α,β-unsaturated imine and methyl vinyl ketone catalyzed by chiral phosphine
Wang, Ge
Rexiti, Rukeya
Sha, Feng
Wu, Xin-Yan
TETRAHEDRON, 2015, 71 (24) : 4255 - 4262
[29] Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoynes and monoenes
Kezuka, S
Tanaka, S
Ohe, T
Nakaya, Y
Takeuchi, R
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02): : 543 - 552
[30] 3,4-DIDEHYDROPYRIDINE PLUS CYCLOPENTADIENE - [2+2] OR [4+2]-CYCLOADDITION
REINECKE, MG
BROWN, ES
CAPEHART, BP
MINTER, DE
FREEMAN, RK
TETRAHEDRON, 1988, 44 (18) : 5675 - 5680

← 1 2 3 4 5 →