✦ LIBER ✦

Synthesis and reactivity of Michael adducts of cyclic β-ketoesters enolates with electrophilic acetylenes

✍ Scribed by Michel Miesch; Gaëtan Mislin; Michel Franck-Neumann

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 228 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01500-7

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✦ Synopsis

The enolates of cyclic ~-ketoesters react with electrophilic acetylenes to give the corresponding Michael adducts in good yields when the reaction is performed in acetone in the presence of catalytic amounts of K2CO 3. The Michael adducts resulting from ethynylmethylketone, when refluxed in toluene in the presence of catalytic amounts of pTsOll, undergo an intrarnolecular aldol reaction leading mainly to bicyclo /n. 3. l ]alkadienones besides Robinson annulation products.

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