Finding Lead Catalytic Systems for a Rare Version of Enantioselective Robinson Annulation: Integration of Fluorogenic Assays in Catalyst Screening.

ABSTRACT: Among the several variants of the highly useful and versatile Robinson annulation, a particular variation that involves ketones reacting with nonenolizable enones, while the α-carbons of the ketones act as nucleophiles at both steps of this cascade process, remains largely unexplored. Moreover, such a catalytic enantioselective reaction is exceptionally rare. While pursuing catalysis of this transformation, we developed two fluorogenic assays that, in combination with other analytic techniques, enabled rapid screening of several sets of catalysts. The first set of polymer-bound aminourea bifunctional organocatalysts was screened using a two-step fluorogenic protocol, designed for slower (e.g., heterogeneous) catalysts. Robinson annulation of acetone with 4'-nitrochalcone formed 3-(4-nitrop

SUBMITTER: Shiloni Y 

PROVIDER: S-EPMC6645050 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature