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Synlett 2012(3): 438-442
DOI: 10.1055/s-0031-1290312
DOI: 10.1055/s-0031-1290312
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Ring Opening of Aminocyclopropyl Ugi Adducts
Further Information
Received
14 November 2011
Publication Date:
19 January 2012 (online)
Publication History
Publication Date:
19 January 2012 (online)
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Abstract
The ring opening of aminocyclopropanes triggered by activation with an intramolecular arylpalladium(II) iodide complex is an interesting strategy for the synthesis of nitrogen heterocycles and a valuable Ugi postcondensation-type transformation. Six- and seven-membered-ring cyclic enamines may be obtained.
Key words
aminocyclopropanes - ring opening - palladium - Ugi - Ugi-Smiles
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References and Notes
The regioselectivity observed with aryl-substituted amino-cyclopropanes may be explained by a productive interaction of the aryl-Pd(II)I intermediate through the less hindered approach of the cyclopropyl ring. Further insights into the potential electronic effects of the aryl moiety should be addressed by comparison with alkyl-substituted cyclo-propanes.