Yi Zhu1, Jianlin Han1, Jiandong Wang2, Norio Shibata2, Mikiko Sodeoka3, Vadim A Soloshonok4,5, Jaime A S Coelho6, F Dean Toste6. 1. School of Chemistry and Chemical Engineering, State Key laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials , Nanjing University , 210093 Nanjing , China. 2. Department of Nanopharmaceutical Sciences & Department of Frontier Materials , Nagoya Institute of Technology , Gokiso, Showa-ku , Nagoya 466-8555 , Japan. 3. Synthetic Organic Chemistry Laboratory , RIKEN, and RIKEN Center for Sustainable Resourse Science , 2-1 Hirosawa , Wako 351-0198 , Japan. 4. Department of Organic Chemistry I, Faculty of Chemistry , University of the Basque Country UPV/EHU , 20018 San Sebastian , Spain. 5. IKERBASQUE, Basque Foundation for Science , 48011 Bilbao , Spain. 6. Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Abstract
New methods for preparation of tailor-made fluorine-containing compounds are in extremely high demand in nearly every sector of chemical industry. The asymmetric construction of quaternary C-F stereogenic centers is the most synthetically challenging and, consequently, the least developed area of research. As a reflection of this apparent methodological deficit, pharmaceutical drugs featuring C-F stereogenic centers constitute less than 1% of all fluorine-containing medicines currently on the market or in clinical development. Here we provide a comprehensive review of current research activity in this area, including such general directions as asymmetric electrophilic fluorination via organocatalytic and transition-metal catalyzed reactions, asymmetric elaboration of fluorine-containing substrates via alkylations, Mannich, Michael, and aldol additions, cross-coupling reactions, and biocatalytic approaches.
New methods for preparation of tailor-made class="Chemical">fluorine-containing class="Gene">pan class="Chemical">compounds are in extremely high demand in nearly every sector of chemical industry. The asymmetric construction of quaternaryC-F stereogenic centers is the most synthetically challenging and, consequently, the least developed area of research. As a reflection of this apparent methodological deficit, pharmaceutical drugs featuring C-F stereogenic centers constitute less than 1% of all fluorine-containing medicines currently on the market or in clinical development. Here we provide a comprehensive review of current research activity in this area, including such general directions as asymmetric electrophilic fluorination via organocatalytic and transition-metal catalyzed reactions, asymmetric elaboration of fluorine-containing substrates via alkylations, Mannich, Michael, and aldol additions, cross-coupling reactions, and biocatalytic approaches.
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