REGIOSELECTIVE CONTROL OF N-ARYL ENAMINONE ALKYLATION

Authors
DUGAT D GARDETTE D GRAMAIN JC PERRIN B
Citation
D. Dugat et al., REGIOSELECTIVE CONTROL OF N-ARYL ENAMINONE ALKYLATION, Bulletin de la Societe chimique de France, 131(1), 1994, pp. 66-70
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
131
Issue
1
Year of publication
1994
Pages
66 - 70
Database
ISI
SICI code
0037-8968(1994)131:1<66:RCONEA>2.0.ZU;2-Q
Abstract
The regioselectivity of the C-alkylation of unsubstituted N-aryl enami nones prepared from cyclohexane-1,3-dione may be controlled by the nat ure of the base used. Our results indicate that monoalkylation is comp letely regioselective; lithium diisopropylamide leads to alpha'-alkyla ted compounds while lithium bis(trimethylsilyl)amide affords gamma-alk ylated products. In contrast, alkylation of alpha'- or gamma-substitut ed compounds always occurs in the alpha'-position regardless of the ba se.