Ethyl trifluoroacetate: A powerful reagent for differentiating amino groups

Article abstract of DOI:10.1016/0040-4039(95)01655-4

Selective protection of primary amines in the presence of secondary amines and monofunctionalization of symmetric primary and secondary diamines using ethyl trifluoroacetate is described. Effective differentiation of primary, secondary and tertiary alkyl-substituted primary amines from one another by ethyl trifluoroacetate acylation is also demonstrated. These results are explained on the basis of steric and electronic effects of the substrate amines.