Aromatization-Driven Cascade [1,5]-Hydride Transfer/Spirocyclization Promoted by Fluorinated Alcohols

被引：61

作者：

Lv, Xintong ^{[1
]}

Hu, Fangzhi ^{[1
]}

Duan, Kang ^{[1
]}

Li, Shuai-Shuai ^{[1
]}

Liu, Qing ^{[3
]}

Xiao, Jian ^{[1
,2
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Agr Univ, Coll Marine Sci & Engn, Qingdao 266109, Peoples R China

[3] Shandong Univ Sci & Technol, Coll Chem & Environm Engn, Qingdao 266590, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 04期

关键词：

PARA-QUINONE METHIDES; C-H FUNCTIONALIZATION; INTRAMOLECULAR HYDRIDE TRANSFER; C(SP(3))-H FUNCTIONALIZATION; BOND FUNCTIONALIZATION; EXPEDIENT SYNTHESIS; INDOLYL ALCOHOLS; DNA ALKYLATION; METAL-FREE; TRANSFER/CYCLIZATION;

D O I：

10.1021/acs.joc.8b02754

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aromatization-driven redox-neutral cascade [1,5]-hydride transfer/spirocyclization and cascade [1,5]-hydride transfer/hydrolysis from para-quinone methide in HFIP were developed. These protocols enabled the synthesis of azaspirocyclohexadienones and ortho-benzylated anilines in good to high yields under mild conditions, featuring room temperature, additive-free, and good functional group tolerance.

引用

页码：1833 / 1844

页数：12

共 95 条

[1] NXS, Morpholine, and HFIP: The Ideal Combination for Biomimetic Haliranium-Induced Polyene Cyclizations [J].

Arnold, Andreas M. ;

Poethig, Alexander ;

Drees, Markus ;

Gulder, Tanja .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (12) :4344-4353

[2] [1,5]-hydride transfer/cyclizations on alkynyl Fischer carbene complexes:: Synthesis of 1,2-dihydroquinolinyl carbene complexes and cascade reactions [J].

Barluenga, Jose ;

Fananas-Mastral, Martin ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6594-6597

[3] Unveiling the "booster effect" of fluorinated alcohol solvents:: Aggregation-induced conformational changes and cooperatively enhanced H-bonding [J].

Berkessel, Albrecht ;

Adrio, Jens A. ;

Huettenhain, Daniel ;

Neudoerfl, Jorg M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8421-8426

[4] Expedient synthesis of tetrahydroquinoline-3-spirohydantoin derivatives via the Lewis acid-catalyzed tert-amino effect reaction [J].

Briones, John F. ;

Basarab, Gregory S. .

CHEMICAL COMMUNICATIONS, 2016, 52 (55) :8541-8544

[5] The Emergence of Quinone Methides in Asymmetric Organocatalysis [J].

Caruana, Lorenzo ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

MOLECULES, 2015, 20 (07) :11733-11764

[6] Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization [J].

Chang, Yong-Zhi ;

Li, Ming-Lei ;

Zhao, Wen-Feng ;

Wen, Xiaoan ;

Sun, Hongbin ;

Xu, Qing-Long .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) :9620-9627

[7] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers [J].

Chauhan, Pankaj ;

Kaya, Ugur ;

Enders, Dieter .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) :888-912

[8]

Chen WJ, 2018, NAT CHEM, V10, P165, DOI [10.1038/NCHEM.2871, 10.1038/nchem.2871]

[9] Hexafluoroisopropanol as a highly versatile solvent [J].

Colomer, Ignacio ;

Chamberlain, Anna E. R. ;

Haughey, Maxwell B. ;

Donohoe, Timothy J. .

NATURE REVIEWS CHEMISTRY, 2017, 1 (11)

[10] Hydrogen Bonding to Hexafluoroisopropanol Controls the Oxidative Strength of Hypervalent Iodine Reagents [J].

Colomer, Ignacio ;

Batchelor-McAuley, Christopher ;

Odell, Barbara ;

Donohoe, Timothy J. ;

Compton, Richard G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8855-8861

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