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Synthesis 2001(10): 1523-1531
DOI: 10.1055/s-2001-16074
DOI: 10.1055/s-2001-16074
PAPER
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation
Further Information
Publication History
Received
21 November 2000
Publication Date:
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