Solid phase strategies: Applications of 2-acetyl-4-nitroindane-1,3- dione as a selective protecting group for primary amines

Article abstract of DOI:10.1016/S0040-4020(98)00365-2

2-Acetyl-4-nitroindane-1,3-dione (1) has been successfully exploited as a primary amine protecting group displaying excellent acid and secondary/tertiary base stability, but which can be removed with 2% hydrazine at ambient temperature. (1) has been condensed with both amino acids and spermidine, affording derivatives which were subsequently utilised in the solid phase synthesis of various peptides and the glutathione-spermidine conjugate trypanothione respectively.