Cross-metathesis of allyl halides with olefins bearing an α-alkoxy amide group

✍ Scribed by Jeong In Yun; Deukjoon Kim; Jongkook Lee

• Book ID: 104098958
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 351 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.02.043

✦ Synopsis

We have examined whether the allyl halide cross-metathesis reaction tolerates a-alkoxy amide groups.

Ruthenium-based catalysts I-III did not catalyze the cross-metathesis of allyl halides in the presence of an a-alkoxy N,N-dimethylamide group to any appreciable extent, but the reaction could tolerate either a bulky N,N-diisopropylamide or Weinreb amide group. In particular, the Grubbs-Hoveyda-Blechert 2nd generation catalyst (III) efficiently catalyzed the cross-metathesis of allyl halides with olefins bearing a Weinreb amide group.