Intramolecular Michael addition of cyclic β-ketoester on conjugated olefinic ketone, a stereoelectronically controlled process

✍ Scribed by Gilles Berthiaume; Jean-François Lavallée; Pierre Deslongchamps

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 214 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85235-1

✦ Synopsis

In the nucleophilic addition on conjugated olefinic ketones (enones), stereoelectronic effects predict that the intermediate enolate should first be generated in a conformation where the newly formed bond is parallel with the II system of the enolatel. Stereoelectronic parameters predict also that the anion of a six-membered S-ketoester should react with an electrophile to generate the alkylated product either in a chair (axial approach) or in a twist-boat (equa-