KOtBu-Catalyzed Synthesis of Isoindole Derivatives from N-Benzyl Amides Bearing an Ortho Alkynyl Group via 1,2-Acyl Shift

被引：2

作者：

Shimazumi, Ryoma ^{[1
]}

Morimoto, Moe ^{[1
]}

Tobisu, Mamoru ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Osaka 5650871, Japan

[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 26期

关键词：

CYCLIZATION; CHEMISTRY;

D O I：

10.1021/acs.orglett.4c02055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we present the catalytic conversion of benzylamides featuring an ortho alkynyl moiety into 1-acylisoindole derivatives via a 1,2-acyl shift. Remarkably, this transformation proceeds without the need for transition-metal catalysts; instead, (KOBu)-Bu-t alone serves as the catalyst. This method enables the efficient synthesis of isoindoles from easily accessible amides with an atom economy of 100%.

引用

收藏

页码：5587 / 5591

页数：5

相关论文

共 26 条

[11] Isoindoles and dihydroisoquinolines by gold-catalyzed intramolecular hydroamination of alkynes [J].

Kadzimirsz, D ;

Hildebrandt, D ;

Merz, K ;

Dyker, G .

CHEMICAL COMMUNICATIONS, 2006, (06) :661-662

[12] A convenient synthesis of N-Boc-protected tert-butyl esters of phenylglycines from benzylamines [J].

Kise, N ;

Ozaki, H ;

Terui, H ;

Ohya, K ;

Ueda, N .

TETRAHEDRON LETTERS, 2001, 42 (43) :7637-7639

[13] Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide [J].

Li, Deng Yuan ;

Shi, Ke Ji ;

Mao, Xiao Feng ;

Zhao, Zheng Le ;

Wu, Xin Yan ;

Liu, Pei Nian .

TETRAHEDRON, 2014, 70 (39) :7022-7031

[14] Visible-Light Induced Isoindoles Formation To Trigger Intermolecular Diels-Alder Reactions in the Presence of Air [J].

Lin, Chao ;

Zhen, Le ;

Cheng, Yong ;

Du, Hong-Jin ;

Zhao, Hui ;

Wen, Xiaoan ;

Kong, Ling-Yi ;

Xu, Qing-Long ;

Sun, Hongbin .

ORGANIC LETTERS, 2015, 17 (11) :2684-2687

[15] Synthetic Transformations through Alkynoxy Palladium Interactions and C-H Activation [J].

Minami, Yasunori ;

Hiyama, Tamejiro .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (01) :67-77

[16] Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes [J].

Morioka, Toshifumi ;

Nakatani, Syun ;

Sakamoto, Yuki ;

Kodama, Takuya ;

Ogoshi, Sensuke ;

Chatani, Naoto ;

Tobisu, Mamoru .

CHEMICAL SCIENCE, 2019, 10 (27) :6666-6671

[17] Unimolecular Fragment Coupling: A New Bond-Forming Methodology via the Deletion of Atom(s) [J].

Shimazumi, Ryoma ;

Tobisu, Mamoru .

JACS AU, 2024, 4 (05) :1676-1695

[18] Palladium-Catalyzed Unimolecular Fragment Coupling of N -Allylamides Bearing a Tethered Nucleophile with the Translocation of an Amide Group [J].

Shimazumi, Ryoma ;

Kodama, Takuya ;

Tobisu, Mamoru .

SYNTHESIS-STUTTGART, 2023, 56 (01) :134-142

[19] Palladium-Catalyzed Unimolecular Fragment Coupling of N-Allylamides via Elimination of Isocyanate [J].

Shimazumi, Ryoma ;

Tanimoto, Riku ;

Kodama, Takuya ;

Tobisu, Mamoru .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (24) :11033-11043

[20] Rhodium-catalyzed intramolecular alkynylsilylation of alkynes [J].

Shintani, Ryo ;

Kurata, Hiroki ;

Nozaki, Kyoko .

CHEMICAL COMMUNICATIONS, 2015, 51 (57) :11378-11381