Remarkable enhancement of nucleophilicity of tin enolates toward nitro- orcyanoalkenes by tetrabutylammonium halides

Authors
Yasuda, M Ohigashi, N Baba, A
Citation
M. Yasuda et al., Remarkable enhancement of nucleophilicity of tin enolates toward nitro- orcyanoalkenes by tetrabutylammonium halides, CHEM LETT, (11), 2000, pp. 1266-1267
Citations number
15
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
11
Year of publication
2000
Pages
1266 - 1267
Database
ISI
SICI code
0366-7022(200011):11<1266:REONOT>2.0.ZU;2-M
Abstract
The reaction of tin enolates with nitroalkenes was effectively catalyzed by tetrabutylammonium bromide (Bu4NBr) to give gamma -nitroketones. When the substituted tin enolates at the beta -carbon in the olefinic moiety were us ed, the diastereoselective addition proceeded through the acyclic transitio n state. Tetrabutylammonium chloride (Bu4NCl) strongly accelerated the reac tion with the cyanoalkene to give the gamma -cyanoketone.