Asymmetric acylation reactions catalyzed by conformationally biased octapeptides

Octapeptides capable of adopting P-hairpin conformations have been found to function as efficient catalysts for the kinetic resolution of certain race mic secondary alcohols. Parallel solid phase synthesis of a series of pepti des with the common feature of the D-Pro-Gly sequence at the turn region (i +3 to i+4) was carried out to yield a family of octapeptide catalysts. The peptides were then screened for their efficiency in a number of enantiosele ctive acylation reactions. (C) 2000 Elsevier Science Ltd. All rights reserv ed.