The Preparation and Intramolecular Radical Cyclisation Reactions of Chiral Oxime Ethers

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.

Keywords

• racemic hydroxylamines
• oxime ester
• intramolecular reactions
• radical cyclizations
• chiral oxime ether