RESEARCH GROUP OF PRIV.-DOZ. DR. U. NUBBEMEYER

Takustr. 3
D-14195 Berlin

since WS 2002/03 prof. at Universität Mainz

E-Mail: udonubb@chemie.fu-berlin.de

FURTHER INFORMATION

• Fachbereichs-Broschüre (Edition 1996) (mostly German !)

KEYWORDS

ABSTRACT

The stereoselective generation of defined optically active tertiary and quaternary carbon centres is still an actual problem in the synthesis of natural- or pharmaceutical important products. The Claisen rearrangement often serves as a key step in the total synthesis of complex structures. A new zwitterionic Aza-Claisen rearrangement was developed in our group to achieve the efficient diastereoselective formation of optically active amides and medium-sized ring-lactams bearing several defined configurated stereogenic centres. The reaction was used to generate key intermediates in natural product synthesis, the enantioselective synthesis of some terpenoids and alkaloids were successfully completed. Actually, the scope and the limitations of several Aza-Claisen rearrangements are studied including stereochemical and mechanistic questions. Furthermore, the rearrangement products with defined stereogenic centres are used for further investigations like iodocyclizations, transannular reactions, radical processes and the total synthesis of optically active alkaloids, prostanoids and amino acids.