Microwave activation of an asymmetric Michael reaction: unexpected behaviour of chiral α-alkoxy imines

✍ Scribed by Cheikhou Camara; Laurent Keller; Françoise Dumas

• Book ID: 104360033
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 180 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00573-1

✦ Synopsis

While it has been previously established that chiral a-alkoxy imines undergo thermal rearrangement at temperatures above 50°C, the microwave activation of the Michael addition between chiral imine 3b and methyl acrylate at 100°C led cleanly to the corresponding Michael adduct 5b without the formation of any rearranged product and with the same regio-and stereoselectivity as the corresponding thermal condensation at 40°C (ee 95%).