Catalytic Asymmetric Intermolecular [3+2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins

被引：15

作者：

Dai, Yating ^{[1
]}

Huang, Hongchun ^{[2
]}

Liang, Shuangshuang ^{[2
]}

Yin, Yanli ^{[1
,3
]}

Ban, Xu ^{[1
]}

Zhao, Xiaowei ^{[2
]}

Jiang, Zhiyong ^{[1
,2
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

[2] Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China

[3] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol, Zhengzhou 451001, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 24期

基金：

中国国家自然科学基金;

关键词：

PHOTOREDOX CATALYSIS; ANNULATION; CYCLOADDITION;

D O I：

10.1021/acs.orglett.3c01585

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective intermolecular [3 + 2] cycloadditionof N-arylcyclopropylamines with 2-aryl acrylates/ketonesandcyclic ketone-derived terminal olefins via asymmetric photoredox catalysisis reported. A dual catalyst system involving DPZ and a chiral phosphoricacid is effective for the transformations, leading to a wide arrayof valuable cyclopentylamines with high yields, ee's, and drs.Among them, elaborate modulation of the ester group of 2-aryl acrylateswas shown to be effective in improving reactivity, thereby enablingthe success of the transformations.

引用

页码：4551 / 4555

页数：5

共 50 条

[31] Native Amide-Directed C(sp3)-H Amidation Enabled by Electron-Deficient RhIII Catalyst and Electron-Deficient 2-Pyridone Ligand
Wakikawa, Takumi
Sekine, Daichi
Murata, Yuta
Bunno, Youka
Kojima, Masahiro
Nagashima, Yuki
Tanaka, Ken
Yoshino, Tatsuhiko
Matsunaga, Shigeki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (12)
[32] Visible light-mediated intermolecular [2+2] photocycloaddition of 1-aryl-2-nitroethenes and olefins
Mohr, Lisa-Marie
Bauer, Andreas
Jandl, Christian
Bach, Thorsten
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (30) : 7192 - 7203
[33] Asymmetric [3+2] Cycloaddition of Olefins with Morita-Baylis-Hillman Carbonates Catalyzed by BINOL-Based Bifunctional Phosphine
Cui, Hai-Lei
Tang, Xue
Li, Meng-Fan
Xu, Xing-Jie
Shi, Yin
SYNLETT, 2019, 30 (07) : 845 - 850
[34] Visible light mediated intermolecular [3+2] annulation of cyclopropylanilines with alkynes
Nguyen, Theresa H.
Maity, Soumitra
Zheng, Nan
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 975 - 980
[35] Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enones
Wilson, JE
Fu, GC
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) : 1426 - 1429
[36] Investigating the Arenyl-Diene Double [3+2] Photocycloaddition Reaction
Penkett, Clive S.
Woolford, Jason A.
Read, Timothy W.
Kahan, Rachel J.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) : 1295 - 1304
[37] Penta-2,4-dien-1-ones by Formal [3+2] Cycloaddition-Rearrangement of Electron-Deficient Diethyl 2-(Dicyanomethylene)malonate with Alkynes
Donckele, Etienne J.
Reekie, Tristan A.
Trapp, Nils
Diederich, Francois
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (04) : 716 - 724
[38] Catalytic Asymmetric Redox-Neutral [3+2] Photocycloadditions of Cyclopropyl Ketones with Vinylazaarenes Enabled by Consecutive Photoinduced Electron Transfer
Wei, Wenhui
Li, Chunyang
Fan, Yifan
Chen, Xiaowei
Zhao, Xiaowei
Qiao, Baokun
Jiang, Zhiyong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (30)
[39] Facile synthesis of spirosubstituted cyclopropanes through reaction of electron-deficient olefins and 1,3-indandione
Huang, Jiamin
Liu, Wenli
Wang, Changqing
Yang, Liu
Cao, Xiaohua
TETRAHEDRON LETTERS, 2020, 61 (04)
[40] Catalytic Asymmetric Dearomatization by Visible-Light-Activated [2+2] Photocycloaddition
Hu, Naifu
Jung, Hoimin
Zheng, Yu
Lee, Juhyeong
Zhang, Lilu
Ullah, Zakir
Xie, Xiulan
Harms, Klaus
Baik, Mu-Hyun
Meggers, Eric
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (21) : 6242 - 6246

← 1 2 3 4 5 →