Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones

被引：32

作者：

Demir, AS ^{[1
]}

Reis, Ö ^{[1
]}

Igdir, AC ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON | 2004年 / 60卷 / 15期

关键词：

enones; oxidation; Mn(OAc)(3); alkenes;

D O I：

10.1016/j.tet.2004.02.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mn(OAc)(3) mediated alpha'-acetoxylation of alpha,beta-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3427 / 3432

页数：6

共 28 条

[1] OXIDATION REACTIONS OF MANGANESE(3) ACETATE .2. FORMATION OF GAMMA-LACTONES FROM OLEFINS AND ACETIC ACID [J].

BUSH, JB ;

FINKBEIN.H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5903-&

[2] CYCLIZATIONS OF UNSATURATED.CR(COX)2 RADICALS - MANGANESE(III) ACETATE OXIDATIVE CYCLIZATIONS OF UNSATURATED ACETOACETATES AND ATOM-TRANSFER CYCLIZATIONS OF UNSATURATED HALOACETOACETATES GIVE THE SAME RADICALS [J].

CURRAN, DP ;

MORGAN, TM ;

SCHWARTZ, CE ;

SNIDER, BB ;

DOMBROSKI, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6607-6617

[3]

De Klein W. J., 1986, ORGANIC SYNTHESIS OX, P261

[4] Role of copper species in the oxidative dimerization of arylboronic acids:: Synthesis of symmetrical biaryls [J].

Demir, AS ;

Reis, Ö ;

Emrullahoglu, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10130-10134

[5] Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one [J].

Demir, AS ;

Aybey, A ;

Sesenoglu, Ö ;

Polat, F .

TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1489-1493

[6] A new and efficient chemoenzymatic route to both enantiomers of 4-hydroxycyclohex-2-en-1-one [J].

Demir, AS ;

Sesenoglu, O .

ORGANIC LETTERS, 2002, 4 (12) :2021-2023

[7] Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones [J].

Demir, AS ;

Hamamci, H ;

Tanyeli, C ;

Akhmedov, IM ;

Doganel, F .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1673-1677

[8] OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID [J].

DEMIR, AS ;

CAMKERTEN, N ;

AKGUN, H ;

TANYELI, C ;

MAHASNEH, AS ;

WATT, DS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2279-2289

[9]

DEMIR AS, 1991, SYNTHESIS-STUTTGART, P235

[10] SYNTHESIS OF QUASSINOIDS .3. OXIDATION OF ENONES TO ALPHA'-ACETOXYENONES USING MANGANESE TRIACETATE [J].

DUNLAP, NK ;

SABOL, MR ;

WATT, DS .

TETRAHEDRON LETTERS, 1984, 25 (51) :5839-5842

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