SYNTHESIS AND REACTIVITY OF MICHAEL ADDUCTS OF CYCLIC BETA-KETOESTERSENOLATES WITH ELECTROPHILIC ACETYLENES

Authors
MIESCH H MISLIN G FRANCKNEUMANN M
Citation
H. Miesch et al., SYNTHESIS AND REACTIVITY OF MICHAEL ADDUCTS OF CYCLIC BETA-KETOESTERSENOLATES WITH ELECTROPHILIC ACETYLENES, Tetrahedron letters, 39(38), 1998, pp. 6873-6876
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
38
Year of publication
1998
Pages
6873 - 6876
Database
ISI
SICI code
0040-4039(1998)39:38<6873:SAROMA>2.0.ZU;2-Y
Abstract
The enolates of cyclic beta-ketoesrers react with electrophilic acetyl enes to give the corresponding Michael adducts in good yields when the reaction is performed in acetone in the presence of catalytic amounts of K2CO3. The Michael adducts resulting from ethynylmethylketone, whe n refluxed in toluene in the presence of catalytic amounts of pTsOH, u ndergo an intramolecular aldol reaction leading mainly to bicyclo [n. 3. 1] alkadienones besides Robinson annulation products. (C) 1998 Else vier Science Ltd. All rights reserved.