Regiochemistry in 1,3-dipolar cycloadditions of the azomethine ylide formed from diethyl aminomalonate and paraformaldehyde.
The azomethine ylide derived from the condensation of diethyl aminomalonate with paraformaldehyde undergoes 1,3-dipolar cycloadditions with acrylate and propiolate derivatives. Contrary to a previous report, these reactions yield mixtures of regioisomers generally favoring the 2,2,3-trisubstituted product. However, the relative quantity of the 2,2,4-trisubstituted product formed increases with an increase in the size of the activating group on the dipolaroplile.
Blazey
Charles M
CM
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
Heathcock
Clayton H
CH
D000818:Animals; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D005557:Formaldehyde / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D011161:Porifera / Q000737:chemistry
D001391:Azo Compounds; D001952:Bridged-Ring Compounds; D008314:Malonates; D011108:Polymers; C410431:sarain A; D005557:Formaldehyde; C057214:diethyl aminomalonate; C003043:paraform