PI-CYCLIZATION REACTIONS OF THIO N-ACYLIMINIUM IONS FOR HETEROCYCLIC SYNTHESIS

Authors
SHEEHAN SM BEALL LS PADWA A
Citation
Sm. Sheehan et al., PI-CYCLIZATION REACTIONS OF THIO N-ACYLIMINIUM IONS FOR HETEROCYCLIC SYNTHESIS, Tetrahedron letters, 39(27), 1998, pp. 4761-4764
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
27
Year of publication
1998
Pages
4761 - 4764
Database
ISI
SICI code
0040-4039(1998)39:27<4761:PROTNI>2.0.ZU;2-2
Abstract
Thio N-acyliminium ions are readily generated from the reaction of thi oamides with bromoacetyl chloride. In the presence of tethered pi-nucl eophiles, cyclization occurs to give S,N-acetals which can be further converted into various alkaloid skeletons. (C) 1998 Elsevier Science L td. All rights reserved.