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

We have examined whether the allyl halide cross-metathesis reaction tolerates α-alkoxy amide groups. Ruthenium-based catalysts I– III did not catalyze the cross-metathesis of allyl halides in the presence of an α-alkoxy N, N-dimethylamide group to any appreciable extent, but the reaction could toler...

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Bibliographic Details
Published in:Tetrahedron letters 2011-04, Vol.52 (16), p.1928-1930
Main Authors: Yun, Jeong In, Kim, Deukjoon, Lee, Jongkook
Format: Article
Language:English
Subjects:
Aliphatic compounds
Allyl halide
Amides
Bearing
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
Cross-metathesis
Exact sciences and technology
General and physical chemistry
Grubbs–Hoveyda–Blechert 2nd generation catalyst
Halides
Olefins
Organic chemistry
Preparations and properties
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Weinreb amide
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Summary:We have examined whether the allyl halide cross-metathesis reaction tolerates α-alkoxy amide groups. Ruthenium-based catalysts I– III did not catalyze the cross-metathesis of allyl halides in the presence of an α-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.02.043