Selective syntheses of cyclobutane-β-aminocarboxylic acid derivatives by the ruthenium complex-catalyzed reaction of allylamines with acrylic compounds

Ruthenium-Catalyzed Reactions for Organic Synthesis

“…Allylamines react with acrylic compounds in the presence of Ru(cod)(cod) catalyst to give cyclobutaneβ-amino acid derivatives (eq 178). 254 The reaction can be rationalized by the formation of the enamines by the ruthenium-catalyzed isomerization and subsequent cycloaddition reaction with acrylic compounds.…”

The Chemistry of 2-Aminocycloalkanecarboxylic Acids

“…Cycloaddition of isobutenylamine 92 with electrophilic olefins such as methyl acrylate gave β-aminocyclobutanecarboxylate 93 as early as in 1961 (Scheme ). This reaction afforded the possibility of a wide variety of substitution on the cyclobutane ring. , Ring opening, ring enlargement, and side-chain reactions of this kind of product have also been studied. , Allylamines react with acryl esters in the presence of ruthenium complexes and N -methylpiperidine at 70 °C for 2 h, to give cyclobutane β-amino acid derivatives of 93 up to 85% yield.

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Ruthenium-Catalyzed S-Propargylation of Thiols Enables the Rapid Synthesis of Propargylic Sulfides

“…Only tertiary amines such as N -methylpiperidine ( 3a , >99%), and triethylamine ( 3a , 92%) were suitable as solvents for the present reaction. These results strongly suggest that amines such as N -methylpiperidine act as both a suitable ligand for an active ruthenium intermediate and a solvent to prevent catalyst poisoning by thiols …”