Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis

被引：242

作者：

Albrecht, Lukasz ^{[1
]}

Dickmeiss, Gustav ^{[1
]}

Acosta, Fabio Cruz ^{[1
]}

Rodriguez-Escrich, Carles ^{[1
]}

Davis, Rebecca L. ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 05期

关键词：

DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; GAMMA-ALKYLATION; ACTIVATION;

D O I：

10.1021/ja211878x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new concept in organocatalysis allowing for the construction of cyclobutanes with four contiguous stereocenters with complete diastereo- and enantiomeric control by a formal [2 + 2]-cycloaddition is presented. The concept is based on simultaneous dual activation of alpha,beta-unsaturated aldehydes and nitroolefins by amino- and hydrogen-bonding catalysis, respectively. A new bifunctional squaramide-based aminocatalyst has been designed and synthesized in order to enable such an activation strategy. The potential and scope of the reaction are demonstrated, and computational studies which account for the stereochemical outcome are presented.

引用

页码：2543 / 2546

页数：4

共 50 条

[41] Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3′-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions
Tan, Wei
Li, Xin
Gong, Yu-Xin
Ge, Meng-Di
Shi, Feng
CHEMICAL COMMUNICATIONS, 2014, 50 (100) : 15901 - 15904
[42] Photoelectrochemical asymmetric dehydrogenative [2+2] cycloaddition between C-C single and double bonds via the activation of two C(sp3)-H bonds
Xiong, Peng
Ivlev, Sergei I.
Meggers, Eric
NATURE CATALYSIS, 2023, 6 (12) : 1186 - 1193
[43] Synthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction
Wu, Lulu
Wang, Youming
Song, Haibin
Tang, Liangfu
Zhou, Zhenghong
Tang, Chuchi
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1053 - 1057
[44] Direct C-H bond arylation of 2-hydroxybenzaldehydes with arylboronic acids via ligand-free palladium catalysis
Weng, Fei
Wang, Chengming
Xu, Bin
TETRAHEDRON LETTERS, 2010, 51 (19) : 2593 - 2596
[45] Asymmetric Formal [3+2] Cycloaddition Reaction of α-Aryl Isocyanoesters with N-Aryl Maleimides by Bifunctional Cinchona Alkaloids-Based Squaramide/AgSbF6 Cooperative Catalysis
Zhao, Mei-Xin
Wei, Deng-Ke
Ji, Fei-Hu
Zhao, Xiao-Li
Shi, Min
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (12) : 2777 - 2781
[46] Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage
Li, Lei
Wu, Xingxing
Zhang, Junliang
CHEMICAL COMMUNICATIONS, 2011, 47 (17) : 5049 - 5051
[47] Enantio- and diastereoselective synthesis of tetrahydrofuro[2,3-b]furan-2(3H)-one derivatives and related oxygen heterocycles via an asymmetric organocatalytic cascade process
Zhao, Wei-Wei
Liu, Yan-Kai
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2358 - 2363
[48] Atroposelective Synthesis of Axially Chiral C2-Arylindoles via Rhodium-Catalyzed Asymmetric C-H Bond Insertion
Liu, Junheng
Li, Qiongya
Shao, Ying
Sun, Jiangtao
ORGANIC LETTERS, 2022, 24 (25) : 4670 - 4674
[49] Selective C(sp2)-H bond functionalization of olefins via visible-light-induced photoredox-quinuclidine dual catalysis
Gu, Xin-Tao
Li, Long-Hai
Wei, Yin
Shi, Min
CHEMICAL COMMUNICATIONS, 2022, 58 (71) : 9954 - 9957
[50] Screening of Potential Inhibitors Targeting the Main Protease Structure of SARS-CoV-2 via Molecular Docking, and Approach with Molecular Dynamics, RMSD, RMSF, H-Bond, SASA and MMGBSA
da Fonseca, Aluisio Marques
Caluaco, Bernardino Joaquim
Madureira, Junilson Martinho Canjanja
Cabongo, Sadrack Queque
Gaieta, Eduardo Menezes
Djata, Faustino
Colares, Regilany Paulo
Neto, Moises Maia
Fernandes, Carla Freire Celedonio
Marinho, Gabrielle Silva
dos Santos, Helcio Silva
Marinho, Emmanuel Silva
MOLECULAR BIOTECHNOLOGY, 2024, 66 (08) : 1919 - 1933

← 1 2 3 4 5 →