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DOI: 10.1055/s-2001-16074
Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation
Publikationsverlauf
Publikationsdatum:
23. September 2004 (online)
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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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The ratio of diastereomers of the picrate salts of 15 and 16 in the crystals was 60:40 by 1H NMR and 54:46 by X-ray, such that confirmation of the major diastereomer by X-ray structure analysis was not certain.