Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling

被引：18

作者：

Kanyiva, Kyalo Stephen ^{[1
]}

Tane, Marina ^{[2
]}

Shibata, Takanori ^{[2
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Global Ctr Sci & Engn, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

[2] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 20期

关键词：

HOFMANN-LOEFFLER TYPE; ORGANIC CATALYSIS; CYCLIC AMINES; IMIDAZOLIDIN-4-ONES; CYCLIZATION; RADICALS; STRATEGIES; AMINATION; FUNCTIONALIZATION; SULFONAMIDES;

D O I：

10.1021/acs.joc.9b01154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp(3))-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp(3))-H bonds were aminated, and various functional groups were tolerated.

引用

页码：12773 / 12783

页数：11

共 73 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] 5-substituted-2-thiohydantoin analogs as a novel class of antitumor agents [J].

AlObaid, AM ;

ElSubbagh, HI ;

Khodair, AI ;

Elmazar, MMA .

ANTI-CANCER DRUGS, 1996, 7 (08) :873-880

[3] One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction [J].

Attorresi, Cecilia I. ;

Bonifazi, Evelyn L. ;

Ramirez, Javier A. ;

Gola, Gabriel F. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (46) :8944-8949

[4]

BAN Y, 1976, CHEM PHARM BULL, V24, P1490

[5] Design and synthesis of 2,3,5-substituted imidazolidin-4-one inhibitors of BACE-1 [J].

Barrow, James C. ;

Rittle, Kenneth E. ;

Ngo, Phung L. ;

Selnick, Harold G. ;

Graham, Samuel L. ;

Pitzenberger, Steven M. ;

McGaughey, Georgia B. ;

Colussi, Dennis ;

Lai, Ming-Tain ;

Huang, Qian ;

Tugusheva, Katherine ;

Espeseth, Amy S. ;

Simon, Adam J. ;

Munshi, Sanjeev K. ;

Vacca, Joseph P. .

CHEMMEDCHEM, 2007, 2 (07) :995-999

[6] Catalytic asymmetric addition of dialkylzinc reagents to α-aldiminoesters [J].

Basra, Sandeep ;

Fennie, Michael W. ;

Kozlowski, Marisa C. .

ORGANIC LETTERS, 2006, 8 (13) :2659-2662

[7] Designing Homogeneous Bromine Redox Catalysis for Selective Aliphatic C-H Bond Functionalization [J].

Becker, Peter ;

Duhamel, Thomas ;

Martinez, Claudio ;

Muniz, Kilian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) :5166-5170

[8] Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3-H Bonds [J].

Becker, Peter ;

Duhamel, Thomas ;

Stein, Christopher J. ;

Reiher, Markus ;

Muniz, Kilian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :8004-8008

[9] INTRAMOLECULAR FUNCTIONALIZATION OF PHOSPHORAMIDATE RADICALS - SYNTHESIS OF 1,4-EPIMINE COMPOUNDS [J].

BETANCOR, C ;

CONCEPCION, JI ;

HERNANDEZ, R ;

SALAZAR, JA ;

SUAREZ, E .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4430-4432

[10] IMIDAZOLIDIN-4-ONES: THEIR SYNTHESES AND APPLICATIONS [J].

Blackmore, Timothy R. ;

Thompson, Philip E. .

HETEROCYCLES, 2011, 83 (09) :1953-1975

← 1 2 3 4 5 6 7 8 →