Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes. A short access to polyenaldehydes

✍ Scribed by Dominique Cahard; Jean-Marie Poirier; Pierre Duhamel

• Book ID: 104259881
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 212 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01544-5

✦ Synopsis

The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a "C-specific reaction occurs. According to the reaction conditions a y ;1,2 or a y ;1,4 coupled product wasselectively obtained with enals. The y ;1,2 reaction provided an efficient prenylation procedure. A short two-step synthesis of retinal is described.