NOVEL SYNTHESES OF MESOIONIC COMPOUNDS AND ALPHA-AMINO-ACID DERIVATIVES FROM ACYLTETRACARBONYLFERRATES

Acyltetracarbonylferrates [1, R1COFe(CO)4-; R1= aryl] react with imidoyl chlorides [2,R2C(C1) = NR3; R2= aryl; R3= aryl or alkyl] in methylene chloride at room temperature to give the mesoionic 1,3-oxazol-5-ones. The latter are convertible to α-amino acid derivatives under gentle conditions. The nature of R1and R2in 1 and 2, respectively, has a significant influence on the reaction course. The formation of the mesoionic heterocycles is proposed to occur via iron-carbene complexes, formed by acyl transfer from the metal to nitrogen. © 1979, American Chemical Society. All rights reserved.