Synthesis of substituted pyrrolidines by sequential radical cyclization and N-acyliminium ion reactions

Authors
Matos, MRPN Afonso, CAM McGarvey, T Lee, P Batey, RA
Citation
Mrpn. Matos et al., Synthesis of substituted pyrrolidines by sequential radical cyclization and N-acyliminium ion reactions, TETRAHEDR L, 40(52), 1999, pp. 9189-9193
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
52
Year of publication
1999
Pages
9189 - 9193
Database
ISI
SICI code
0040-4039(199912)40:52<9189:SOSPBS>2.0.ZU;2-K
Abstract
Readily available N-acyl-2-pyrrolines are converted into functionalized alp ha-alkoxy-beta-iodopyrrolidines by N-iodosuccinimide promoted alcohol addit ion to the enamine group. These compounds are readily cyclized using a sodi um cyanoborohydride-catalytic tributylstannane system affording functionali zed pyrrolidines in good yields. The cyclized products undergo N-acyliminiu m ion reactions, such as BF3. OEt2 mediated addition of allyltrimethylsilan e. (C) 1999 Elsevier Science Ltd. All rights reserved.