An organocatalytic asymmetric Nazarov cyclization.

ABSTRACT: An organocatalytic asymmetric Nazarov cyclization of diketoesters that proceeds by means of a dual activation mechanism has been developed. Screening of a number of catalysts led to a new thiourea that incorporates a primary amino group. The method gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high or very high enantiomeric excess. A brief and very convenient synthesis of the acyclic diketoester starting materials through nucleophilic addition to a ketene is also described.

SUBMITTER: Basak AK 

PROVIDER: S-EPMC2903437 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature