Stereoselective aza-Diels-Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines.
Highly diastereoselective Lewis acid mediated aza-Diels-Alder reactions of chiral auxiliary derivatized 2H-azirines have been accomplished for the first time, yielding bi and tri-cyclic heterocyclic compounds, comprising aziridine and tetrahydropyridine substructures, in up to 97% de; with the absolute stereochemistry of the major product confirmed by X-ray crystallography.
Timén
Asa Sjöholm
AS
Department of Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden.
Fischer
Andreas
A
Somfai
Peter
P