+ Translate
+ Most Popular
The pigeon tick (Argas reflexus): its biology, ecology, and epidemiological aspects
Prevalence of hemoglobin abnormalities in Kebili (Tunisian South)
Lipogranuloma: a preventable complication of dacryocystorhinostomy
Value of basal plasma cortisol assays in the assessment of pituitary-adrenal insufficiency
Bees from the Belgian Congo. The acraensis group of Anthophora
Placing gingival retraction cord
Total serum IgE, allergy skin testing, and the radioallergosorbent test for the diagnosis of allergy in asthmatic children
Acariens plumicoles Analgesoidea parasites des oiseaux du Maroc
Injuries of terminal phalanges of the fingers in children
Biology of flowering and nectar production in pear (Pyrus communis)
Das Reliktvorkommen der Aspisviper (Vipera aspis L.) im Schwarzwald
Hydrological modelling of drained blanket peatland
Pathologic morphology and clinical significance of the anomalous origin of the left circumflex coronary artery from the right coronary artery. General review and autopsy analysis of 30 cases
Cyto genetic analyses of lymphocyte cultures after exposure to calcium cyclamate
Axelrodia riesei, a new characoid fish from Upper Rio Meta in Colombia With remarks concerning the genus Axelrodia and description of a similar, sympatric, Hyphessobrycon-species
Favorable evolution of a case of tuberculosis of pancreas under antibiotic action
RIFM fragrance ingredient safety assessment, Valencene, CAS Registry Number 4630-07-3
Parenteral microemulsions: an overview
Temperate pasture: management for grazing and conservation
Evaluation of a new coprocessed compound based on lactose and maize starch for tablet formulation
Thermal expansion and cracking of three confined water-saturated igneous rocks to 800C
Revision of the genera of the tribe Stigmoderini (Coleoptera: Buprestidae) a discussion of phylogenetic relationships
Anal tuberculosis. Report of a case
Gastric tuberculosis in the past and present
Adaptive responses of the cardiovascular system to prolonged spaceflight conditions: assessment with Holter monitoring

Peracid oxidation of 4 isoxazolines as a method for the preparation of alpha beta unsaturated carbonyl compounds

Peracid oxidation of 4 isoxazolines as a method for the preparation of alpha beta unsaturated carbonyl compounds

Journal of Organic Chemistry 53(10): 2238-2245

ISSN/ISBN: 0022-3263

DOI: 10.1021/jo00245a021

A study of the MCPBA peracid oxidation of a series of 4-isoxazolines has been carried out. A variety of isoxazolines were synthesized by treating nitrones with electron-deficient alkynes. An alternate approach involves dipolar cycloaddition of nitrones with activated allenes followed by a subsequent base-catalyzed isomerization of the initially formed cycloadduct. Treatment of the 5-exo-methyleneisoxazolidine derived from the reaction of N-benzylidenemethylamine N-oxide and (phenylsulfonyl)propadiene with LDA followed by .gamma.-alkylation also produced substituted 4-isoxazolines. The peracid oxidation of the isoxazoline ring afforded .alpha.,.beta.-unsaturated carbonyl compounds in excellent yield. Reductive cleavage of the sulfonyl group of some of the enones was achieved by initial protection of the carbonyl functionally by cyanosilylation using trimethylsilyl cyanide, and this was followed by aluminum-amalgam reduction. The cycloaddition-oxidation procedure provides an attractive route to synthesize .alpha.,.beta.-unsaturated ketones since it avoids acidic or basic conditions.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 006080931

Download citation: RISBibTeXText

Related references

A Convenient Method for the Preparation of (Z)-alpha,beta-Unsaturated Carbonyl Compounds. Journal of Organic Chemistry 61(8): 2908-2910, 1996

Method of producing alpha-halo-alpha,beta-saturated carbonyl compounds from the corresponding alpha,beta-unsaturated compounds. Official Gazette of the United States Patent and Trademark Office Patents 1257(5), 2002

Unprecedented direct oxygen atom transfer from hypervalent oxido-lambda(3)-iodanes to alpha,beta-unsaturated carbonyl compounds: synthesis of alpha,beta-epoxy carbonyl compounds. Organic Letters 2(19): 2923-2926, 2000

Lewis acid controlled regioselective 1,2 and 1,4 reaction of alpha,beta-unsaturated carbonyl compounds with Ti(IV) enolates derived from alpha-diazo beta-keto carbonyl compounds. Angewandte Chemie 41(15): 2773-2776, 2002

Hypervalent iodine oxidation of alpha beta unsaturated carbonyl compounds. Chemical and Pharmaceutical Bulletin 35(2): 570-577, 1987

Isoxazoline oxidation. An efficient method for the preparation of α,β-unsaturated carbonyl compounds. Tetrahedron Letters 28(9): 913-916, 1987

Formation of alpha,beta-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols. Tetrahedron Letters 35(38): 7097-7098, 1994

FT-IR kinetic and product study of the Br-radical initiated oxidation of alpha, beta-unsaturated organic carbonyl compounds. Atmospheric Environment 33(18): 2969-2979, 1999

A convenient preparation of 3,3,3-trifluoro-1-propynylamines and their Lewis acid catalyzed reaction with carbonyl compounds leading to (z)-alpha-(trifluoromethyl)-alpha,beta-unsaturated amides. Journal of Organic Chemistry 66(10): 3442-3448, 2001

Oxidation of allylic alcohols to alpha,beta-unsaturated carbonyl compounds with aqueous hydrogen peroxide under organic solvent-free conditions. Chemical Communications 2007(42): 4399-4400, 2007

A novel and efficient method for the preparation of α-hydroxyimino carbonyl compounds from α,β-unsaturated carbonyl compounds with butyl nitrite and phenylsilane catalyzed by a cobalt(II) complex. Bulletin of the Chemical Society of Japan 64(10): 2948-2953, 1991

Highly efficient aza-Baylis-Hillman reaction of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate: Lewis base effects and a convenient method to synthesize alpha,beta-unsaturated beta-amino carbonyl compounds. Journal of Organic Chemistry 69(2): 417-425, 2004

Pyrethroid chemistry reactive alpha beta unsaturated keto aldehydes from peracid oxidation oxidative photodecomposition and metabolism of 5 benzyl 3 furylmethyl derivatives. Journal of Agricultural and Food Chemistry 33(4): 622-625, 1985

A facile synthesis of alpha,beta-difluoro-alpha,beta-unsaturated carbonyl compounds by use of molecular fluorine addition. Tetrahedron Letters 36(37): 6705-6708, 1995

A GaCl3-catalyzed [4+1] cycloaddition of alpha,beta-unsaturated carbonyl compounds and isocyanides leading to unsaturated gamma-lactone derivatives. Journal of the American Chemical Society 125(26): 7812-7813, 2003