α-Bromination of linear enals and cyclic enones

被引：13

作者：

Bovonsombat, Pakorn ^{[1
]}

Rujiwarangkul, Rungkarn ^{[1
]}

Bowornkiengkai, Thanathip ^{[1
]}

Leykajarakul, Juthamard ^{[1
]}

机构：

[1] Mahidol Univ Int Coll, Salaya Campus, Nakhon Pathom 73170, Thailand

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 49期

关键词：

D O I：

10.1016/j.tetlet.2007.10.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile alpha-bromination of cyclic enones and linear enals involving N-bromosuccinimide and 1-2 equiv of pyridine-N-oxide is reported herein. alpha-Bromination of linear enals was found to proceed with double bond geometry retention. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8607 / 8610

页数：4

共 34 条

[1] Stereoelectronic and steric control in chiral cyclohexane synthesis toward (-)-tetrodotoxin [J].

Bamba, M ;

Nishikawa, T ;

Isobe, M .

TETRAHEDRON, 1998, 54 (24) :6639-6650

[2] CONCERNING THE FORMATIONS OF ALPHA-IODOENONES [J].

BOVONSOMBAT, P ;

ANGARA, GJ ;

MCNELIS, E .

TETRAHEDRON LETTERS, 1994, 35 (37) :6787-6790

[3] Stereoselective preparation of phosphine oxides via a 2,3-sigmatropic shift of allylic diphenylphosphinites [J].

Demay, S ;

Harms, K ;

Knochel, P .

TETRAHEDRON LETTERS, 1999, 40 (27) :4981-4984

[4] Formations of alpha-iodoenones by iodine and catalytic amounts of amines [J].

Djuardi, E ;

Bovonsombat, P ;

McNelis, E .

SYNTHETIC COMMUNICATIONS, 1997, 27 (14) :2497-2503

[5] MECHANISMS OF ELIMINATION-REACTIONS .39. STERIC AND ELECTRONIC EFFECTS ON STEREOCHEMISTRY IN ELIMINATIONS FROM PRIMARY ALKYLTRIMETHYLAMMONIUM SALTS [J].

DOHNER, BR ;

SAUNDERS, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) :245-247

[6] SYNTHESIS OF PENTACYCLO[4.3.0.02,5.03,8.04,7]NONANE (HOMOCUBANE) AND SOME OF ITS DERIVATIVES [J].

DUNN, GL ;

DIPASQUO, VJ ;

HOOVER, JRE .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1454-+

[7]

GUACIARO MA, 1978, TETRAHEDRON LETT, P4661

[8] MODIFIED STILLE COUPLING UTILIZING ALPHA-IODOENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW .

TETRAHEDRON LETTERS, 1992, 33 (07) :919-922

[9] DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW ;

WOVKULICH, PM ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1992, 33 (07) :917-918

[10] REACTION OF BENZENESELENINYL CHLORIDE WITH OLEFINS IN THE PRESENCE OF A LEWIS ACID - A NOVEL ONE-STEP VINYLIC CHLORINATION [J].

KAMIGATA, N ;

SATOH, T ;

YOSHIDA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (02) :449-454

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