Aza-Claisen rearrangement

What is aza-Claisen rearrangement?

The aza-Claisen rearrangement is a specific variation of Claisen rearrangement and Belluš-Claisen rearrangement that involves the conversion of allylenamines and allylamides into γ,δ-unsaturated imines. While typically requiring high temperatures to proceed, this rearrangement can be conducted at lower temperatures when a Lewis acid is included or when transforming an amide enolate. Interestingly, when utilizing the amide enolate approach, the stereochemistry of the product varies according to the geometric isomerism of the amide enolate.

Aza-Claisen rearrangement
aza-Claisen rearrangement


R.K. Hill, N.W. Gilman, “A nitrogen analog of the Claisen rearrangement” Tetrahedron Lett. 1967, 8, 1421-1423.