Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D. Issue 34 (12th June 2015)

• Record Type: Journal Article
• Authors: Shih, Jiun‐Le; Nguyen, Thien S.; May, Jeremy A.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 34(2015)
• Page Start: 9931
• Page End: 9935
• Publication Date: 2015-06-12
• Subjects: bis‐aryl stereocenters -- enantioselective catalysis -- heterocycles -- organocatalysis -- trifluoroborate salts; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201503528
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Bis‐heteroaryl or bis‐aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration. Abstract : Fluoride has to go : Bis‐heteroaryl or bis‐aryl stereocenters are formed through an organocatalytic enantioselective conjugate addition using heteroaryl or aryl trifluoroborate salts, respectively, as nucleophiles. Control experiments suggest that fluoride dissociation in the anhydrous conditions is necessary. The reaction was applied toward the synthesis of discoipyrrole D, an inhibitor of DDR2‐dependent migration of BR5 fibroblasts.