Regioselectivity and diastereoselectivity of three-component reaction of α-amino acid, dialkyl acetylenedicarboxylates and 2-arylidene-1,3-indanediones

The 1,3-dipolar cycloaddition of active azomethine ylide, which were generated in situ from addition reaction of alpha-amino acids with dialkyl acetylenedicarboxylates, with 2-arylidene-1,3-indanediones showed versatile regioselectivity and diastereoselectivity. The reaction of sarcosine and glycine afforded one kind of functionalized spiro[indene-2,3 '-pyrrolidines]. The other primary alpha-amino acids such as alanine, phenylalanine and leucine gave another kind of regioisomeric spiro[indene-2,3 '-pyrrolidines]. The cyclic alpha-amino acids resulted in the corresponding spiro[indene-2,2 '-pyrrolizines] and [indene-2,6 '-pyrrolo[1,2-c]thiazoles].