A novel two-step preparation of enaminoketones by amination of α,β-unsaturated ketones with methoxyamine

被引：36

作者：

Seko, S ^{[1
]}

Tani, N ^{[1
]}

机构：

[1] Sumitomo Chem Co Ltd, Organ Synth Res Lab, Osaka 5691093, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(98)01801-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Methoxyaminoketones, derived from the addition of methoxyamine to 1,3-diaryl-2-propen-1-one, underwent base-induced beta-elimination to furnish the corresponding enaminoketones in good to moderate yields. The reaction conditions and substituents on the substrates significantly influenced the selectivity in the production of enaminoketone and/or aziridineketone. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8117 / 8120

页数：4

共 15 条

[1]

BARTOLI G, 1990, SYNTHESIS-STUTTGART, P895

[2] THE PHYSICAL AND CHEMICAL PROPERTIES OF THE METHYLHYDROXYLAMINES [J].

BISSOT, TC ;

PARRY, RW ;

CAMPBELL, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (04) :796-800

[3]

BLATT AH, 1939, J AM CHEM SOC, V61, P3494

[4] PALLADIUM-ASSISTED FUNCTIONALIZATION OF OLEFINS - A NEW AMINATION OF ELECTRON-DEFICIENT OLEFINS [J].

BOZELL, JJ ;

HEGEDUS, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2561-2563

[5]

BRAIBANTE MEF, 1994, SYNTHESIS-STUTTGART, P898

[6] ONE-STEP SYNTHESIS OF AZIRIDINES BY THE MICHAEL TYPE ADDITION OF FREE SULFIMIDES - PREPARATION AND ABSOLUTE-CONFIGURATION OF OPTICALLY-ACTIVE ACYLAZIRIDINES [J].

FURUKAWA, N ;

YOSHIMURA, T ;

OHTSU, M ;

AKASAKA, T ;

OAE, S .

TETRAHEDRON, 1980, 36 (01) :73-80

[7]

GREENHILL JV, 1977, CHEM SOC REV, V6, P277, DOI 10.1039/cs9770600277

[8] COMPUTER-ASSISTED MECHANISTIC EVALUATION OF ORGANIC-REACTIONS .12. PKA PREDICTIONS FOR ORGANIC-COMPOUNDS IN ME2SO [J].

GUSHURST, AJ ;

JORGENSEN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3513-3522

[9]

HONMA T, 1977, HETEROCYCLES, V6, P1985

[10] PALLADIUM(II)-CATALYZED AMIDATION OF ALKENES [J].

HOSOKAWA, T ;

TAKANO, M ;

KUROKI, Y ;

MURAHASHI, SI .

TETRAHEDRON LETTERS, 1992, 33 (44) :6643-6646

← 1 2 →