Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

被引：23

作者：

Chandrasekhar, B.

Ahn, Sewon

Ryu, Jae-Sang ^{[1
]}

机构：

[1] Ewha Womans Univ, Coll Pharm, 52 Ewhayeodae Gil, Seoul 03760, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

ONE-POT SYNTHESIS; ALKYNYLZINC REAGENTS; ASYMMETRIC ADDITION; NITRONES; 2,3-DIHYDROISOXAZOLES; ACYLAZIRIDINES; N-(PROPARGYLIC)HYDROXYLAMINES; CYCLOADDITION; REARRANGEMENT; ISOXAZOLINES;

D O I：

10.1021/acs.joc.6b01499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.

引用

收藏

页码：6740 / 6749

页数：10

相关论文

共 33 条

[1] ISOXAZOLES .22. NEW SYNTHESIS OF 4-ISOXAZOLINES AND THEIR THERMAL CONVERSION INTO PYRROLES [J].

ADACHI, I ;

HARADA, K ;

MIYAZAKI, R ;

KANO, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (01) :61-69

[2] Reduction of 2,3-dihydroisoxazoles to β-amino ketones and β-amino alcohols [J].

Aschwanden, P ;

Kvaerno, L ;

Geisser, RW ;

Kleinbeck, F ;

Carreira, EM .

ORGANIC LETTERS, 2005, 7 (25) :5741-5742

[3] Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].

Aschwanden, P ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (15) :2331-2333

[4] Efficient synthesis of (S)-3,4-dihydro-2-pivaloyloxymethyl-2H-pyrrole 1-oxide [J].

Busqué, F ;

de March, P ;

Figueredo, M ;

Font, J ;

Gallagher, T ;

Milán, S .

TETRAHEDRON-ASYMMETRY, 2002, 13 (04) :437-445

[5] Tandem addition/cyclization of alkynylzinc reagents to enantiopure 2-tert-butyl-3,5-dimethyl-2,3-dihydroimidazol-4-one N-oxide:: Potential precursors of quaternary α-amino acids [J].

Cantagrel, F ;

Pinet, S ;

Gimbert, Y ;

Chavant, PY .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (13) :2694-2701

[6] Synthesis of (±)-Tetrapetalone A-Me Aglycon [J].

Carlsen, Peter N. ;

Mann, Tyler J. ;

Hoveyda, Amir H. ;

Frontier, Alison J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (35) :9334-9338

[7] Gold-catalyzed propargylic substitutions: Scope and synthetic developments [J].

Debleds, Olivier ;

Gayon, Eric ;

Vrancken, Emmanuel ;

Campagne, Jean-Marc .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :866-877

[8] A Dual Gold-Iron Catalysis for a One-Pot Synthesis of 2,3-Dihydroisoxazoles from Propargylic Alcohols and N-Protected Hydroxylamines [J].

Debleds, Olivier ;

Dal Zotto, Christophe ;

Vrancken, Emmanuel ;

Campagne, Jean-Marc ;

Retailleau, Pascal .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1991-1998

[9] SYNTHESIS OF N-BENZYL NITRONES [J].

DONDONI, A ;

FRANCO, S ;

JUNQUERA, F ;

MERCHAN, F ;

MERINO, P ;

TEJERO, T .

SYNTHETIC COMMUNICATIONS, 1994, 24 (18) :2537-2550

[10] Silyl triflate-accelerated additions of catalytically generated zinc acetylides to N-phenyl nitrones [J].

Downey, C. Wade ;

Maxwell, Erin N. ;

Confair, Danielle N. .

TETRAHEDRON LETTERS, 2014, 55 (35) :4959-4961

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