A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis(phenol).

ABSTRACT: We report a catalytic approach to the synthesis of a key intermediate on the synthetic route to a pharmaceutical drug candidate in single enantiomer form. In particular, we illustrate the discovery process employed to arrive at a powerful, peptide-based asymmetric acylation catalyst. The substrate this catalyst modifies represents a remarkable case of desymmetrization, wherein the enantiotopic groups are separated by nearly a full nanometer, and the distance between the reactive site and the pro-stereogenic element is nearly 6 A. Differentiation of enantiotopic sites within molecules that are removed from the prochiral centers by long distances presents special challenges to the field of asymmetric catalysis. As the distance between enantiotopic sites increases within a substrate, so too m

SUBMITTER: Lewis CA 

PROVIDER: S-EPMC2669675 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature