Highly stereoselective syntheses of five- and seven-membered ring heterocycles from ylides generated by catalytic reactions of styryldiazoacetates with aldehydes and imines.
[reaction--see text] Styryldiazoacetates are effective reactants for ylide formation that results in the formation of dihydropyrroles and dihydroazepines with high stereocontrol and in high yields.
Doyle
M P
MP
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA. mdoyle@u.arizona.edu
Hu
W
W
Timmons
D J
DJ
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003979:Diazonium Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
D000085:Acetates; D000447:Aldehydes; D001381:Azepines; D003979:Diazonium Compounds; D007097:Imines; D011758:Pyrroles; D013343:Styrenes