Highly Regio- and Diastereoselective Palladium-Catalyzed Allylic Substitution. Synthesis of 3-(2-Aminobutylidene)- 4-arylazetidin-2-ones

The palladium‐catalyzed benzylamine attack to a particular allylic moiety, the 3‐alkenyl‐3‐bromoazetidin‐2‐one is herein reported. This reaction shows interesting mechanistic aspects and allows us to introduce in one step and under high regio‐ and stereocontrol the amino function in the C3 side chai...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2005-05, Vol.347 (6), p.833-838
Main Authors: Cardillo, Giuliana, Fabbroni, Serena, Gentilucci, Luca, Perciaccante, Rossana, Tolomelli, Alessandra
Format: Article
Language:English
Subjects:
allylic substitution
azetidinone
diastereoselectivity
palladium
regioselectivity
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Summary:The palladium‐catalyzed benzylamine attack to a particular allylic moiety, the 3‐alkenyl‐3‐bromoazetidin‐2‐one is herein reported. This reaction shows interesting mechanistic aspects and allows us to introduce in one step and under high regio‐ and stereocontrol the amino function in the C3 side chain of non‐conventional β‐lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404385