Acyclic oxyiminium ions. Mannich reactions and addition of Grignard reagents

Authors
Grigg, R Rankovic, Z Thoroughgood, M
Citation
R. Grigg et al., Acyclic oxyiminium ions. Mannich reactions and addition of Grignard reagents, TETRAHEDRON, 56(40), 2000, pp. 8025-8032
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
40
Year of publication
2000
Pages
8025 - 8032
Database
ISI
SICI code
0040-4020(20000929)56:40<8025:AOIMRA>2.0.ZU;2-X
Abstract
Acyclic oxyiminium ion generation from secondary hydroxylamines (4a,b and 6 a,b) and formaldehyde in the presence of acetic acid is reported. Trapping these electrophiles with 2-methyl furan, pyrrole or indole affords a series of novel O-benzyl tertiary hydroxylamines in good to excellent yield. Benz otriazole mediated synthetic methodology has also been successfully develop ed to generate oxyiminium ions which react with Grignard reagents, to give novel O-benzyl tertiary hydroxylamines. (C) 2000 Elsevier Science Ltd. All rights reserved.