XY–ZH systems as potential 1,3-dipoles. Part 6. Metallo-1,3-dipoles. Cycloadditions of divalent metal complexes of glycine and alanine imines to electronegative olefins

Autor:	Ronald Grigg, Visuvanathar Sridharan, S. Thianpatanagul
Rok vydání:	1986
Předmět:	chemistry.chemical_compound Stereospecificity chemistry Stereochemistry 1 3-Dipolar cycloaddition chemistry.chemical_element Zinc Nuclear magnetic resonance spectroscopy Acrylonitrile Weak base Methyl acrylate Medicinal chemistry Cycloaddition
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1669-1675
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19860001669
Popis:	Copper(II), zinc(II), and cadmium(II) complexes of imines derived from α-oxo acids and glycine or alanine undergo stereospecific cycloaddition at room temperature to 1,2-disubstituted electronegative olefins in the presence of weak base. Corresponding reactions of lead(II) complexes give insoluble cycloadducts. In contrast, the reactions of the same metallo imines with methyl acrylate, phenyl vinyl sulphone, and acrylonitrile frequently give mixtures of regio- and stereo-isomers. These mixtures are shown to arise by stereoisomerisation of initial cycloadducts formed by a 4π+ 2π concerted cycloaddition of intermediate metallo-1,3-dipoles.
Databáze:	OpenAIRE
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