The Preparation and Intramolecular Radical Cyclisation Reactions of Chiral Oxime Ethers



Document title: The Preparation and Intramolecular Radical Cyclisation Reactions of Chiral Oxime Ethers
Journal: Journal of the Brazilian Chemical Society
Database: PERIÓDICA
System number: 000310732
ISSN: 0103-5053
Authors: 1

2
Institutions: 1Leicester University, Department of Chemistry, Leicester, Leicestershire. Reino Unido
2Merck, Sharp and Dohme, Harlow, Essex. Reino Unido
Year:
Season: Ago
Volumen: 9
Number: 4
Pages: 389-395
Country: Brasil
Language: Inglés
Document type: Artículo
Approach: Experimental
English abstract Chiral oxime ether 2 and Oxime ester 4 have been prepared by alkylation and esterification of the oxime 1. Racemic hydroxylamine 6 and chiral hydroxylamine 10 have been synthesised from N-hydroxysuccinimide and the corresponding alcohol in the presence of diethylazodicarboxylate, the two products were converted into the oxime ethers 7 and 11 respectively. The intramolecular radical cyclisation reactions of these oxime ethers and esters has been studied, successful reaction was observed to produce alkyl hydroxylamines 3, 8 and 12
Portuguese abstract O éter-oxima quiral 2 e o éster-oxima 4 foram preparados para alquilação e esterificação da oxina 1. Hidroxiamina racêmica 6 e a hidroxiamina 10 foram sintetisadas a partir de N-hidroxipucanimida e o álcool correspondente na presença de di etil azodicarboxilato, e os dois produtos convertidos nos éteres-oximas 7 e 11 respectivamente. As reações de ciclização radicalar intramoleculares desses éteres e ésteres-oxima foram estudadas; a formação das alquil hidróxi-aminas 3, 8 e 12 foi observada nas reações bem sucedidas
Disciplines: Química
Keyword: Química orgánica,
Hidroxilaminas racémicas,
Ester de oxima,
Reacciones intramoleculares,
Ciclización radical,
Moléculas quirales,
Eter de oxima
Keyword: Chemistry,
Organic chemistry,
Racemic hydroxylamines,
Oxime ester,
Intramolecular reactions,
Radical cyclization,
Chiral molecules,
Oxime ether
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