Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination

• Authors: Coralie De Schutter, Emory University; O Sari, Emory University; Steven Coats, Emory University; Franck Amblard, Emory University; Raymond Schinazi, Emory University
• Journal Title: Journal of Organic Chemistry
• Volume: Volume 82, Number 24
• Publisher: American Chemical Society | 2017-12-15, Pages 13171-13178
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1021/acs.joc.7b02245
• Subjects: Chemistry, Organic; Chemistry, Biochemistry; Health Sciences, Pharmacology; Chemistry, Pharmaceutical
• Keywords: Science & Technology; Physical Sciences; Chemistry, Organic; Chemistry; Catalytic enantioselective fluorination; Assymetric fluorination; Hepatitis C; Diastereoselective; Beta-ketoesters; Aldol reaction; Condensation; Complexes; Efficient replication; PSI-6130

Abstract

A novel and efficient route for the preparation of (2S)-2-chloro-2-fluorolactone 29 is described. This approach takes advantage of a highly efficient diastereoselective electrophilic fluorination reaction (94% yield; >50:1 dr)