The regiospecific synthesis of the N(π)-allyl and the N(τ)-allyl derivatives of N(α)-tert-butoxycarbonyl-histidine is described. The DCC-mediated coupling of N(α>-tert-butoxycarbonyl-N(π)-allyl-(L)-histidine with (L)-prolinamide, used as a test reaction to probe the extent of racemization during coupling processes, was found to occur with good (ca. 97%) conservation of enantiomeric purity. Three methods have been devised, all of them based on catalytic palladium π-allyl chemistry, for the selective removal under mild conditions of the N-imidazolic allyl groups. Finally it is shown that the allyl group at N(τ)-position may be used as a temporary protection in the synthesis of N(π)-substituted derivatives of histidine.