Regioselective electrophilic oxidation of a 5-amino-endo-tricyclo[5.2.1.0(2,6)]decenyl enaminone. Synthesis of a novel heterocyclic compound

Authors
Ramesh, NG Klunder, AJH Zwanenburg, B
Citation
Ng. Ramesh et al., Regioselective electrophilic oxidation of a 5-amino-endo-tricyclo[5.2.1.0(2,6)]decenyl enaminone. Synthesis of a novel heterocyclic compound, TETRAHEDR L, 42(43), 2001, pp. 7707-7709
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
43
Year of publication
2001
Pages
7707 - 7709
Database
ISI
SICI code
0040-4039(20011022)42:43<7707:REOOA5>2.0.ZU;2-M
Abstract
An unexpected tandem regioselective oxidation and cyclization of 5-((S)-2'- hydroxymethylpyrrolidin-1'-yl)-endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-o nes 7 is reported. The reaction proceeds smoothly to afford novel tetracycl ic compounds 8 and 9 in good yield, The structure of 8 was established by s ingle-crystal X-ray analysis. Surprisingly, the C8-C9 norbornene double bon d remains intact under these oxidative conditions. (C) 2001 Elsevier Scienc e Ltd. All rights reserved.