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
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
Affiliation:
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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Cite this article as:
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
DOI https://dx.doi.org/10.2174/157017806777828420 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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