Asymmetric Acylation Reactions Catalyzed by Conformationally Biased Octapeptides

Octapeptides capable of adopting β-hairpin conformations have been found to function as efficient catalysts for the kinetic resolution of certain racemic secondary alcohols. Parallel solid phase synthesis of a series of peptides 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 enantioselective acylation reactions.