Intramolecular Carbolithiation of Aromatic N-Allyl-N-(2-Lithioallyl)Amines:Reinvestigation of the Mechanism and Synthesis of Functionalized Pyrrolidines

Author(s): Francisco J. Fananas, Delia Miguel, M Pilar Castroviejo, Roberto Sanz.

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 6 , 2006

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Abstract:

The intramolecular carbolithiation reactions of aromatic N-allyl-N-(2-lithioallyl)amines have been studied in detail. Although we have initially proposed a 6-endo ring closure for these substrates, we have found that the course of these processes starts with a 5-exo cyclization reaction. Interestingly, 3- functionalized-4-methylenepyrrolidines have been synthesized from simple starting materials.

Keywords: pyrrolidines, 5-exo cyclizations, organolithiums, Carbolithiation reactions

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Article Details

VOLUME: 3
ISSUE: 6
Year: 2006
Page: [470 - 476]
Pages: 7
DOI: 10.2174/157017806777828420
Price: $58