Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs
Top Cited Papers
- 2 April 2018
- journal article
- review article
- Published by American Chemical Society (ACS) in Chemical Reviews
- Vol. 118 (7), 3887-3964
- https://doi.org/10.1021/acs.chemrev.7b00778
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.Funding Information
- RIKEN
- Asahi Glass Foundation
- Eusko Jaurlaritza
- Japan Society for the Promotion of Science (JP16H01017, JP16H01142)
- Japan Science and Technology Agency
- National Natural Science Foundation of China (21761132021)
- National Institute of General Medical Sciences (R35 GM118190)
- Funda??o para a Ci?ncia e a Tecnologia (SFRH/BPD/100433/2014)
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