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The Preparation and Intramolecular Radical Cyclisation Reactions of Chiral Oxime Ethers

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journal contribution
posted on 15.01.2016, 15:37 by Susan E. Booth, Paul R. Jenkins, Christopher J. Swain
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. 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.

Funding

We thank the S.E.R.C. and Merck, Sharp and Dohme for a studentship to S.E.B. and the S.E.R.C. Mass spectrometry Service at Swansea University.

History

Citation

Journal of the Brazilian Chemical Society 9(4), 389-395

Version

VoR (Version of Record)

Published in

Journal of the Brazilian Chemical Society 9(4)

Publisher

Sociedade Brasileira de Química, SBQ

issn

0103-5053

eissn

1678-4790

Available date

15/01/2016

Publisher version

http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000400012&lng=en&nrm=iso&tlng=en

Language

en