Samarium(II) iodide-mediated intramolecular aldol-type cyclization

Authors
Sono, M Nakashiba, Y Nakashima, K Takaoka, S Tori, M
Citation
M. Sono et al., Samarium(II) iodide-mediated intramolecular aldol-type cyclization, HETEROCYCLE, 54(1), 2001, pp. 101-104
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
1
Year of publication
2001
Pages
101 - 104
Database
ISI
SICI code
0385-5414(20010101)54:1<101:SIIAC>2.0.ZU;2-L
Abstract
The alpha -substituted alpha,beta -epoxy ketone having a formyl group in th e molecule reacted with samarium(II) iodide to afford cyclized spiro ketone s formed by an intramolecular aldol-type reaction. However, in the presence of proton source the ratio of spiro products decreased and the yield of hy drindanone increased. The alpha -substituted alpha,beta -unsaturated cyclop entenone derivative smoothly cyclized into the same hydrindanone.