NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

被引：5

作者：

Ji, Hong ^{[1
]}

Zou, Juan ^{[2
]}

Mou, Chengli ^{[2
]}

Liu, Yonggui ^{[1
]}

Ren, Shi-Chao ^{[1
]}

Chi, Yonggui Robin ^{[1
,3
]}

机构：

[1] Guizhou Univ, Natl Key Lab Green Pesticide, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China

[2] Guiyang Coll Tradit Chinese Med, Sch Pharm, Guiyang 550025, Peoples R China

[3] Nanyang Technol Univ, Sch Chem Chem Engn & Biotechnol, Singapore 637371, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 42期

关键词：

CYCLOADDITIONS; ANNULATION;

D O I：

10.1039/d3cc00999h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp(3) (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).

引用

页码：6351 / 6354

页数：4

共 50 条

[21] Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
Ahire, Milind M.
Mhaske, Santosh B.
ACS OMEGA, 2017, 2 (10): : 6598 - 6604
[22] Efficient Synthesis of γ-Keto Sulfones by NHC-Catalyzed Intermolecular Stetter Reaction
Bhunia, Anup
Yetra, Santhivardhana Reddy
Bhojgude, Sachin Suresh
Biju, Akkattu T.
ORGANIC LETTERS, 2012, 14 (11) : 2830 - 2833
[23] NHC-catalyzed activation of α,β-unsaturated N-acyltriazoles: an easy access to dihydropyranones
Ni, Qijian
Xiong, Jiawen
Song, Xiaoxiao
Raabe, Gerhard
Enders, Dieter
CHEMICAL COMMUNICATIONS, 2015, 51 (78) : 14628 - 14631
[24] NHC-Catalyzed Atroposelective Acylation of Phenols: Access to Enantiopure NOBIN Analogs by Desymmetrization
Lu, Shenci
Poh, Si Bei
Rong, Zi-Qiang
Zhao, Yu
ORGANIC LETTERS, 2019, 21 (15) : 6169 - 6172
[25] On the Role of CO2 in NHC-Catalyzed Oxidation of Aldehydes
Chiang, Pei-Chen
Bode, Jeffrey W.
ORGANIC LETTERS, 2011, 13 (09) : 2422 - 2425
[26] Mechanism and regio- and stereoselectivity in an NHC-catalyzed Mannich/lactamization domino reaction
Li, Yan
Li, Zhilin
Zhang, Zhiqiang
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (10) : 6204 - 6212
[27] Mechanistic Study of Pd/NHC-Catalyzed Sonogashira Reaction: Discovery of NHC-Ethynyl Coupling Process
Eremin, Dmitry B.
Boiko, Daniil A.
Kostyukovich, Alexander Yu.
Burykina, Julia V.
Denisova, Ekaterina A.
Anania, Mariarosa
Martens, Jonathan
Berden, Giel
Oomens, Jos
Roithova, Jana
Ananikov, Valentine P.
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (67) : 15672 - 15681
[28] NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides
Youn, So Won
Song, Hyoung Sub
Park, Jong Hyub
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2388 - 2393
[29] A DFT Study on the NHC-Catalyzed Reaction of Enals with Aminoacrylates: Mechanism, Regioselectivity, and Stereoselectivity
Li, Yan
Xiao, Junjie
Kang, Yanlong
Zhang, Zhiqiang
JOURNAL OF PHYSICAL CHEMISTRY A, 2024, 128 (49): : 10544 - 10554
[30] Mechanism, Chemoselectivity, and Stereoselectivity of an NHC-Catalyzed Reaction of Aldehydes and Hydrazones: A DFT Study
Li, Yan
Kang, Yanlong
Xiao, Junjie
Zhang, Zhiqiang
JOURNAL OF PHYSICAL CHEMISTRY A, 2024, 128 (22): : 4483 - 4492

← 1 2 3 4 5 →