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

Francisco   J.   Fananas; Delia      Miguel; M Pilar      Castroviejo; Roberto      Sanz

doi:10.2174/157017806777828420

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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Letters in Organic Chemistry

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

Volume: 3 Issue: 6

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

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

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.

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Fananas J. Francisco, Miguel Delia, Castroviejo M Pilar and Sanz Roberto, Intramolecular Carbolithiation of Aromatic N-Allyl-N-(2-Lithioallyl)Amines:Reinvestigation of the Mechanism and Synthesis of Functionalized Pyrrolidines, Letters in Organic Chemistry 2006; 3 (6) . https://dx.doi.org/10.2174/157017806777828420