The Aza‐Cope/Mannich Reaction
2011
Because of their ability to rapidly build molecular complexity, reactions that construct several carbon-carbon bonds are of special value in organic synthesis. Among these transformations, cascade reactions form several bonds by an orchestrated sequence in which the first bond-forming step reveals functionality that allows subsequent bond forming transformations. In 1979 such a sequence for the synthesis of 3-acylpyrrolidines and azacyclic structures that contain this unit was reported. This reaction is now commonly called the aza-Cope/Mannich reaction, a [3,3]-sigmatropic rearrangement of an unsaturated iminium cation generates the iminium ion and enol that are participants in a subsequent intramolecular Mannich reaction.
The aza-Cope/Mannich reaction has not been the subject of comprehensive review. This chapter covers the common version of the transformation discussed above along with the formation of 3-acylpyrrolidines by a related base-promoted cascade sequence.
Keywords:
Aza-Cope/Mannich reactions;
1- Aminobut-3-en-2-ols;
Amine alkylation;
Iminium ion;
Vinyl substituents;
Stereochemistry;
Mechanisms;
Condensation;
Solvent;
Acid;
Ring enlarging;
Rearrangements;
Base-promoted reactions;
Experimental procedures
Keywords:
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