Nonstereospecific 1,3-dipolar cycloadditions of azomethine ylides and enamines

Authors
Bohm, T Weber, A Sauer, J
Citation
T. Bohm et al., Nonstereospecific 1,3-dipolar cycloadditions of azomethine ylides and enamines, TETRAHEDRON, 55(31), 1999, pp. 9535-9558
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
31
Year of publication
1999
Pages
9535 - 9558
Database
ISI
SICI code
0040-4020(19990730)55:31<9535:N1COAY>2.0.ZU;2-T
Abstract
The combination of electron-poor azomethine ylides 3 (AMY-I) or 4 (AMY-II) with electron-rich enamines 5 results in nonstereospecific 1,3-dipolar cycl oadditions, which are LUMOdipole,-HOMOdipolarophile controlled reactions. T his phenomenon can be explained only by a two-step mechanism via zwitterion ic intermediates. (C) 1999 Elsevier Science Ltd. All rights reserved.