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

ABSTRACT: The 1,3-dipolar cycloaddition of active azomethine ylide, which were generated in situ from addition reaction of ?-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 ?-amino acids such as alanine, phenylalanine and leucine gave another kind of regioisomeric spiro[indene-2,3'-pyrrolidines]. The cyclic ?-amino acids resulted in the corresponding spiro[indene-2,2'-pyrrolizines] and [indene-2,6'-pyrrolo[1,2-c]thiazoles].

SUBMITTER: Chen L

PROVIDER: S-EPMC5622111 | biostudies-other | 2017 Sep

REPOSITORIES: biostudies-other

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

Chen Liang L Sun Jing J Huang Ying Y Zhang Yu Y Yan Chao-Guo CG

Scientific reports 20170929 1

The 1,3-dipolar cycloaddition of active azomethine ylide, which were generated in situ from addition reaction of α-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 α-amino acids such as alanine, phenylalanine and leucine gave another kind of regioisomeric spiro[indene-2,3'-pyrrol ...[more]

PMID: 28963495

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