Synthesis of CF3-Containing Spiro-[Indene-Proline] Derivatives via Rh(III)-Catalyzed C-H Activation/Annulation

被引：1

作者：

Bubnova, Alexandra S. ^{[1
]}

Vorobyeva, Daria V. ^{[1
]}

Godovikov, Ivan A. ^{[1
]}

Smol'yakov, Alexander F. ^{[1
]}

Osipov, Sergey N. ^{[1
]}

机构：

[1] AN Nesmeyanov Inst Organoelement Cpds, Russian Acad Sci, 28-1 Vavilova Str, Moscow 119334, Russia

来源：

MOLECULES | 2023年 / 28卷 / 23期

基金：

俄罗斯科学基金会;

关键词：

C-H activation; spiro cyclization; rhodium catalysis; fluorinated proline derivatives; 3+2 ANNULATION; ALKYNES; BENZAMIDES; FUNCTIONALIZATION; ACTIVATION; SULTAMS; OXIDANT; ACCESS;

D O I：

10.3390/molecules28237809

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient method of accessing new CF3-containing spiro-[indene-proline] derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]-annulation reaction of 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to act as a directing group in the selective activation of the aromatic C-H bond.

引用

页数：14

共 39 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL REVIEWS, 2015, 115 (11) :5301-5365

[3] Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C-H Functionalization and Spiroannulation [J].

Chidipudi, Suresh Reddy ;

Burns, David J. ;

Khan, Imtiaz ;

Lam, Hon Wai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :13975-13979

[4] Synthesis of Isoquinolines via Rh(III)-Catalyzed C-H Activation Using Hydrazone as a New Oxidizing Directing Group [J].

Chuang, Sheng-Chieh ;

Gandeepan, Parthasarathy ;

Cheng, Chien-Hong .

ORGANIC LETTERS, 2013, 15 (22) :5750-5753

[5]

Dillard L.W., 2011, WIPO Patent, Patent No. [2011106414A1, 2011106414, WO2011106414]

[6] New development in the enantioselective synthesis of spiro compounds [J].

Ding, Aishun ;

Meazza, Marta ;

Guo, Hao ;

Yang, Jung Woon ;

Rios, Ramon .

CHEMICAL SOCIETY REVIEWS, 2018, 47 (15) :5946-5996

[7] Rhodium-Catalyzed Spirocyclic Sultam Synthesis by [3+2] Annulation with Cyclic N-Sulfonyl Ketimines and Alkynes [J].

Dong, Lin ;

Qu, Chuan-Hua ;

Huang, Ji-Rong ;

Zhang, Wei ;

Zhang, Qian-Ru ;

Deng, Jin-Gen .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) :16537-16540

[8] Controlling Destiny through Chemistry: Small-Molecule Regulators of Cell Fate [J].

Firestone, Ari J. ;

Chen, James K. .

ACS CHEMICAL BIOLOGY, 2010, 5 (01) :15-34

[9] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies [J].

Guimond, Nicolas ;

Gorelsky, Serge I. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) :6449-6457

[10] Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C-H/N-H Activation [J].

Hyster, Todd K. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10565-10569

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