Elsevier

Tetrahedron Letters

Volume 38, Issue 15, 14 April 1997, Pages 2763-2766
Tetrahedron Letters

5-exo versus 6-endo intramolecular carbolithiation of N-allyl-N-(2-lithioallyl)amines

https://doi.org/10.1016/S0040-4039(97)00465-6Get rights and content

Abstract

N-Allyl-N-(2-lithioallyl)amines undergo intramolecular carbometallation via 5-exo or 6-endo addition. The course of the reaction depends on the nitrogen electron density. 3-Functionalized-4-methylenepyrrolidines can be synthesized.

The ring mode closure in the carbolithiation of N-allyl-N-(2-lithioallyl)amines depends on the nature of the susbtituents bound to the susbtituents bound to the nitrogen atom.

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