Abstract
Fluorinated organic compounds, in particular those containing
nitrogen atoms, are popular targets in medicinal chemistry. They
are obtained through chemical synthesis, usually by employing small,
fluorinated molecules as starting building blocks. This account
focuses on the reactivity and synthetic applications of different
types of fluorinated building blocks. It summarizes recent methodologies
developed in our and other laboratories for the synthesis of a variety
of nitrogen-containing organofluorine compounds.
1 Introduction
2 Fluorinated Imidoyl Halides
2.1 Reaction of Fluorinated Imidoyl Chlorides with Enolates: Synthesis
of Fluorinated β-Amino Acids
2.2 Reaction of Fluorinated Imidoyl Chlorides with Sulfoxides
3 Fluorinated α-Imino Esters and Imines
3.1 Fluorinated α-Imino Esters
3.2 Fluorinated Aldimines and Ketimines
4 Fluorinated Acrylic Acid Derivatives
5 Fluorinated gem -Difluoroalkynes
6 Fluorinated Nitriles
6.1 Synthesis of Fluorinated Uracils
6.2 Synthesis of Fluorinated Pyrimidin-2(1H )-ones
7 Fluorinated β-Dicarbonylic Compounds
8 Miscellaneous
8.1 Tandem Ring-Closing Metathesis-Isomerization
8.2 β-Amino-α-trifluoromethyl Alcohols
9 Conclusion
Key words
fluorine - nitrogen - asymmetric synthesis - diastereoselectivity - regioselectivity
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