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

被引：100

作者：

Aschwanden, P ^{[1
]}

Frantz, DE ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 15期

关键词：

D O I：

10.1021/ol006095r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel cyclization reaction of propargylic N-hydroxylamines to 2,3,5-trisubstituted 2,3-dihydroisoxazoles in the presence of catalytic amounts (10 mol %) of Znl(2) and DMAP is reported. The methodology provides a mild new approach to this useful class of substituted heterocycles that complements extant methods. The unique reactivity of the propargylic N-hydroxylamine substrates in the presence of Zn(II) and DMAP may have additional applications in other, related alkyne cyclization reactions.

引用

页码：2331 / 2333

页数：3

共 32 条

[1] ISOXAZOLES .23. SYNTHESIS OF N-SUBSTITUTED 4-ISOXAZOLINES AND THEIR CONVERSION INTO 2-ACYLAZIRIDINES
ADACHI, I
MIYAZAKI, R
KANO, H
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (01) : 70 - 77
[2] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[3] 2-5
[4] Baldwin J., 1978, CIBA F SYMP, V53, P85
[5] 5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE
BALDWIN, JE
CUTTING, J
DUPONT, W
KRUSE, L
SILBERMAN, L
THOMAS, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 736 - 738
[6] APPROACH VECTOR ANALYSIS - STEREOCHEMICAL APPROACH TO REACTIVITY
BALDWIN, JE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 738 - 741
[7] RULES FOR RING-CLOSURE
BALDWIN, JE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
[8] A reiterative synthesis of trans-fused polypyrans via tungsten pentacarbonyl-promoted alkynol endocyclization
Bowman, JL
McDonald, FE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) : 3680 - 3682
[9] The application of nitrido manganese reagents to the synthesis of protected N-methyl D-fucosamine
Carreira, EM
Hong, J
Du Bois, J
Tomooka, CS
[J]. PURE AND APPLIED CHEMISTRY, 1998, 70 (05) : 1097 - 1103
[10] A NITRONE-BASED CYCLOADDITION APPROACH TO THE SYNTHESIS OF THE GLYCOSYL SYSTEM OF NOGALOMYCIN, MENOGARIL, AND THEIR CONGENERS
DESHONG, P
LI, W
KENNINGTON, JW
AMMON, HL
LEGINUS, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) : 1364 - 1373

← 1 2 3 4 →