Citation
I. Coldham et al., Stereoselective synthesis of pyrrolidines and pyrrolizidines by intramolecular carbolithiation, SYNTHESIS-S, (10), 2001, pp. 1523-1531
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881
→ ACNP
Issue
10
Year of publication
2001
Pages
1523 - 1531
Database
ISI
SICI code
0039-7881(200108):10<1523:SSOPAP>2.0.ZU;2-6
Abstract
Methods for the preparation of substituted homoallylic amines and their con
version to pyrrolidines or pyrrolizidines are described. N-Alkylation of a
variety of homoallylic secondary amines with (tributylstannyl)methyl methan
esulfonate and subsequent tinlithium exchange, generates organolithium spec
ies that undergo intramolecular carbolithiation (anionic cyclization). High
stereoselectivities in the cyclization, particularly for the formation of
2,4-disubstituted pyrrolidines, are obtained.