Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation

Iain Coldham; Richard Hufton; Kathy N. Price; Richard E. Rathmell; David J. Snowden; Graham P. Vennall

doi:10.1055/s-2001-16074

PAPER

Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation

Iain Coldham*, Richard Hufton, Kathy N. Price, Richard E. Rathmell, David J. Snowden, Graham P. Vennall
School of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK
Fax: +44(1392)263434; e-Mail: I.Coldham@exeter.ac.uk;

Abstract

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Abstract

Methods for the preparation of substituted homoallylic amines and their conversion to pyrrolidines or pyrrolizidines are described. N-Alkylation of a variety of homoallylic secondary amines with (tributylstannyl)methyl methanesulfonate and subsequent tin-lithium exchange, generates organolithium species that undergo intramolecular carbolithiation (anionic cyclization). High stereoselectivities in the cyclization, particularly for the formation of 2,4-disubstituted pyrrolidines, are obtained.

Key words

amines - carbanions - cyclizations - lithiation - heterocycles

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References

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