A new protocol for the Baylis–Hillman reaction: the reaction of iminium salts prepared in situ with methyl acrylate

✍ Scribed by Najmedin Azizi; Mohammad R Saidi

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 421 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00803-1

✦ Synopsis

In situ prepared iminium salts are very effective electrophiles in Baylis-Hillman reactions and react with methyl acrylate in the presence of a catalytic amount of a tertiary amine at ambient temperatures to afford the corresponding Baylis-Hillman adducts. The product undergoes conjugated addition with (trimethylsilyl)dialkylamines to give the diamine 5 in good yields.