Iron(III)-Catalyzed Consecutive Aza-Cope−Mannich Cyclization: Synthesis of trans-3,5-Dialkyl Pyrrolidines and 3,5-Dialkyl-2,5-dihydro-1H-pyrroles

An efficient alkene aza-Cope−Mannich cyclization between 2-hydroxy homoallyl tosylamine and aldehydes in the presence of iron(III) salts to obtain 3-alkyl-1-tosyl pyrrolidines in good yields is described. The process is based on the consecutive generation of a γ-unsaturated iminium ion, 2-azonia-[3,...

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Bibliographic Details
Published in:Organic letters 2010-11, Vol.12 (22), p.5334-5337
Main Authors: Carballo, Rubén M, Purino, Martín, Ramírez, Miguel A, Martín, Víctor S, Padrón, Juan I
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Catalysis
Chlorides - chemistry
Cyclization
Ferric Compounds - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Stereoisomerism
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Summary:An efficient alkene aza-Cope−Mannich cyclization between 2-hydroxy homoallyl tosylamine and aldehydes in the presence of iron(III) salts to obtain 3-alkyl-1-tosyl pyrrolidines in good yields is described. The process is based on the consecutive generation of a γ-unsaturated iminium ion, 2-azonia-[3,3]-sigmatropic rearrangement, and further intramolecular Mannich reaction. Iron(III) salts are also shown to be excellent catalysts for the new aza-Cope−Mannich cyclization using 2-hydroxy homopropargyl tosylamine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102372c