Aminoreduktone – Untersuchungen an Verbindungen mit dem C-Gerüst des Dimedons und mit sekundären Aminen als Bausteinen
✍ Scribed by Kurt Schank; Rebecca Glock; Carlo Lick
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- German
- Weight
- 338 KB
- Volume
- 88
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Aminoreductones – Investigations on Species Containing the Carbon Arrangement of Dimedone and Secondary Amines as Building Blocks
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 CC 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.