✦ LIBER ✦
Chemie und Stereochemie der Iridoide, XVII. Palladium-katalysierte Substitution an Hexaacetylaucubin
✍ Scribed by Weinges, Klaus ;Ziegler, Hans Jürgen
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 298 KB
- Volume
- 1991
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Chemistry and Stereochemistry of Iridoids, XVII. – Palladium‐Catalysed Substitution of Hexaacetylacubin
Acetoxy groups, in allylic position, can be replaced by nucleophiles in a palladium‐catalysed reaction. The reaction of hexaacetylaucubin (2) with piperidine or benzylamine regioselectively gives the crystalline, N‐containing iridoidglucosides 3 and 4. With the anion of diemethyl malonate, 5 was obtained along with the byproduct 7. Adding triethylammonium formate as a hydride donor, then the reaction gives 6; a reaction mechanism is discussed.