Enantioselective thiourea-catalyzed cationic polycyclizations.

ABSTRACT: A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-pi interactions are a principal determinant of enantioselectivity.

SUBMITTER: Knowles RR 

PROVIDER: S-EPMC2989498 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature