Practical epoxidation of alpha,beta-unsaturated ketones with tetra-n-butylammonium peroxydisulfate

被引：24

作者：

Kim, YH

Hwang, JP

Yang, SG

机构：

[1] Department of Chemistry, Korea Adv. Inst. Sci. and Technol., Taejon

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(97)00521-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-beta-Unsaturated ketones reacted with tetra-n-butylammonium peroxydisulfate in the presence of hydrogen peroxide and base in acetonitrile at 25 degrees c to give the corresponding epoxides in excellent yields. (C) 1997 Elsevier Science Ltd.

引用

页码：3009 / 3012

页数：4

共 21 条

[1] A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS [J].

ACENA, JL ;

ARJONA, O ;

DELAPRADILLA, RF ;

PLUMET, J ;

VISO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6419-6424

[2] STEREOCONTROLLED TOTAL SYNTHESIS OF "1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL [J].

BAGGIOLINI, EG ;

IACOBELLI, JA ;

HENNESSY, BM ;

BATCHO, AD ;

SERENO, JF ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3098-3108

[3] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF SUBSTITUTED PHENYL GLYCIDIC ESTERS [J].

BAURES, PW ;

EGGLESTON, DS ;

FLISAK, JR ;

GOMBATZ, K ;

LANTOS, I ;

MENDELSON, W ;

REMICH, JJ .

TETRAHEDRON LETTERS, 1990, 31 (45) :6501-6504

[4]

BENZUIDENHOUDT BCB, 1987, TETRAHEDRON LETT, V28, P4857

[5]

Brukem S. D., 1984, J AM CHEM SOC, V106, P4558

[6] FACILE CLEAVAGE OF N,N-DIMETHYLHYDRAZONES TO KETONES USING TETRABUTYLAMMONIUM PEROXYDISULFATE [J].

CHOI, HC ;

KIM, YH .

SYNTHETIC COMMUNICATIONS, 1994, 24 (16) :2307-2311

[7]

CHOI HC, 1996, HETEROATOM CHEM, V6, P333

[8] ITERATIVE 3-CARBON ANNELATION - A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-HIRSUTIC ACID C [J].

GREENE, AE ;

LUCHE, MJ ;

DEPRES, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2435-2439

[9] STUDIES OF VITAMIN-D (CALCIFEROL) AND ITS ANALOGS .30. THERMAL [1,7]-SIGMATROPIC HYDROGEN SHIFTS - STEREOCHEMISTRY, KINETICS, ISOTOPE EFFECTS, AND PI-FACIAL SELECTIVITY [J].

HOEGER, CA ;

JOHNSTON, AD ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4690-4698

[10] POLYMER-SUPPORTED POLY(AMINO ACIDS) AS NEW ASYMMETRIC EPOXIDATION CATALYST OF ALPHA,BETA-UNSATURATED KETONES [J].

ITSUNO, S ;

SAKAKURA, M ;

ITO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :6047-6049

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