Synthesis of γ-lactams via Ru(II)-Pheox-catalyzed regioselective intramolecular Csp3-H insertion of diazoacetamides

被引：4

作者：

Fujii, Takuji ^{[1
]}

Huong Dang Thi Thu ^{[1
]}

Iwasa, Seiji ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, Tempaku Cho, Toyohashi, Aichi 4418580, Japan

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 37期

关键词：

C-H Insertion; gamma-Lactam; Ruthenium; Carbene; Diazoacetamide; C-H INSERTION; CARBENE INSERTION; BETA-LACTAMS; CYCLOPROPANATION; CATALYSTS; OLEFINS; CONSTRUCTION; COMPLEXES; CARBON; BOND;

D O I：

10.1016/j.tetlet.2020.152276

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, gamma-lactam derivatives are obtained in high yield via highly regioselective intramolecular Csp(3)-H insertion reactions of alpha-diazoacetamides catalyzed by a rac-Ru(II)-Pheox complex. The catalytic system is applicable to a wide range of diazoacetamides under mild conditions to produce the corresponding gamma-lactams. (C) 2020 Elsevier Ltd. All rights reserved.

引用

收藏

页数：4

相关论文

共 50 条

[1] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex [J].

Abu-Elfotoh, Abdel-Moneim ;

Phomkeona, Kesiny ;

Shibatomi, Kazutaka ;

Iwasa, Seiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) :8439-8443

[2] Desymmetrization by Asymmetric Copper-Catalyzed Intramolecular C-H Insertion Reactions of α-Diazo-β-oxosulfones [J].

Brouder, Thomas A. ;

Slattery, Catherine N. ;

Ford, Alan ;

Khandavilli, U. B. Rao ;

Skorepova, Eliska ;

Eccles, Kevin S. ;

Lusi, Matteo ;

Lawrence, Simon E. ;

Maguire, Anita R. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :7543-7563

[3]

Buchner E., 1885, BER DTSCH CHEM GES, V18, P2377, DOI DOI 10.1002/CBER.188501802119

[4] Synthesis of N-(2,3,4,5,6-Pentafluorobenzyloxy)-γ-lactams by Rhodium-Catalyzed Cyclization of Diazo Amides [J].

Budny, Marcin ;

Nowak, Magdalena ;

Wojtczak, Andrzej ;

Wolan, Andrzej .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) :6361-6365

[5] Rh(II) catalysed intramolecular C-H insertion of diazo substrates in water: a simple and efficient approach to catalyst reuse [J].

Candeias, NR ;

Gois, PMP ;

Afonso, CAM .

CHEMICAL COMMUNICATIONS, 2005, (03) :391-393

[6] Biologically active γ-lactams: synthesis and natural sources [J].

Caruano, J. ;

Muccioli, G. G. ;

Robiette, R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (43) :10134-10156

[7] Enantioselective Cyclopropanation of a Wide Variety of Olefins Catalyzed by Ru(II)-Pheox Complexes [J].

Chanthamath, Soda ;

Iwasa, Seiji .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2080-2090

[8] Ru(II)-Pheox catalyzed N-H insertion reaction of diazoacetamides: synthesis of N-substituted α-aminoamides [J].

Chanthamath, Soda ;

Thongjareun, Songkharm ;

Shibatomi, Kazutaka ;

Iwasa, Seiji .

TETRAHEDRON LETTERS, 2012, 53 (36) :4862-4865

[9] The synthesis of baclofen and GABOB via Rh(II) catalyzed intramolecular C-H insertion of α-diazoacetamides [J].

Chen, ZL ;

Chen, ZY ;

Jiang, YZ ;

Hu, WH .

TETRAHEDRON, 2005, 61 (06) :1579-1586

[10] Probing the mechanism of the anomalous intramolecular C-H insertion reaction of rhodium carbenoids by analysis of kinetic isotope effects [J].

Clark, JS ;

Wong, YS ;

Townsend, RJ .

TETRAHEDRON LETTERS, 2001, 42 (35) :6187-6190

← 1 2 3 4 5 →