21428-71-7Relevant academic research and scientific papers
Aminoreductones - Investigations on species containing the carbon arrangement of dintedone and secondary amines as building blocks
Schank, Kurt,Glock, Rebecca,Lick, Carlo
, p. 3174 - 3199 (2007/10/03)
The ozonation of 3-(sec-amino)-5,5-dimethylcyclohex-2-en-1-ones 4 was compared with the corresponding acyloxylations by diacylperoxides 5, making accessible 3-(sec-amino)-reductones 9. Both types of oxygenation also led to higher-oxygenated six-ring carbocyclic products (7, 8, 17), ozonation being a minor reaction path, in addition to C=C cleavage. The corresponding 2-(sec-amino)reductones 34 were generated via aminolysis of the iodonium intermediate 44 (Scheme 13), and their reductive behavior against t-BuOCl and 3-chloroperbenzoic acid (MCPBA) as oxidizing agents was compared. Attempts to generate the corresponding reductone 5,5-dimethyl-2,3-dimorpholin-4-ylcyclohex- 2-en-1-one (45) were unsuccessful (Scheme 13). Instead, the corresponding iodonium intermediate 44 suffered a Favorskii-like regioselective ring contraction during aminolysis, followed by autoxidation. These unexpected reactions were confirmed by separate experiments.
