Aza-Diels–Alder reaction in fluorinated alcohols. A one-pot synthesis of tetrahydroquinolines

✍ Scribed by Maria Vittoria Spanedda; Vu Dinh Hoang; Benoit Crousse; Danièle Bonnet-Delpon; Jean-Pierre Bégué

• Book ID: 104252659
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 246 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02558-3

✦ Synopsis

Hexafluoroisopropanol and trifluoroethanol are found to promote imino-Diels-Alder reactions of the N-aryl aldimine 1 with alkyl vinyl ethers to afford the corresponding tetrahydroquinolines in good yields without Lewis acid under mild and neutral conditions. The reaction is also efficient in a three component process from aldehyde, amine and vinyl ethers.