To Professor Kenji Uneyama and Professor Donald J. Burton for their great contribution to fluoroorganic chemistry

Abstract

Pyrrolidines and their derivatives are of great interest in medicinal chemistry and organic synthesis. Fluoropyrrolidines and (fluoroalkyl)pyrrolidines have been utilized in the preparation of medicinal drugs and also as organocatalysts. The synthesis of such compounds is achieved through the fluorination of pyrrolidine derivatives or by multistep synthesis from already containing fluoroalkyl precursors.

1 Introduction

1.1 General Interest of Fluorine-Containing Pyrrolidines

1.2 Fluoroalkylpyrrolidines and the Gauche Effect

2 Fluoropyrrolidines

2.1 3-Fluoropyrrolidines

2.2 3,3- and 3,4-Difluoropyrrolidines

2.3 3,3,4-Trifluoropyrrolidines

2.4 3,3,4,4-Tetrafluoropyrrolidines

3 (Difluoromethyl)- and (Trifluoromethyl)pyrrolidines

3.1 2-(Trifluoromethyl)pyrrolidines

3.2 3- and 4-(Trifluoromethyl)pyrrolidines

3.3 2-(Difluoromethyl)pyrrolidines

3.4 3- and 4-(Difluoromethyl)pyrrolidines

4 (Monofluoroalkyl)pyrrolidines

4.1 2-(Monofluoromethyl)pyrrolidines

4.2 2-(Monofluoroalkyl)pyrrolidines

4.3 2-(Monofluoroalkenyl)pyrrolidines

5 Conclusion

Pyrrolidines and their derivatives are of great interest in medicinal chemistry and organic synthesis. Fluoropyrrolidines and (fluoroalkyl)pyrrolidines have been utilized in the preparation of medicinal drugs and also as organocatalysts. The synthesis of such compounds is achieved through the fluorination of pyrrolidine derivatives or by multistep synthesis from already containing fluoroalkyl precursors.

1 Introduction

1.1 General Interest of Fluorine-Containing Pyrrolidines

1.2 Fluoroalkylpyrrolidines and the Gauche Effect

2 Fluoropyrrolidines

2.1 3-Fluoropyrrolidines

2.2 3,3- and 3,4-Difluoropyrrolidines

2.3 3,3,4-Trifluoropyrrolidines

2.4 3,3,4,4-Tetrafluoropyrrolidines

3 (Difluoromethyl)- and (Trifluoromethyl)pyrrolidines

3.1 2-(Trifluoromethyl)pyrrolidines

3.2 3- and 4-(Trifluoromethyl)pyrrolidines

3.3 2-(Difluoromethyl)pyrrolidines

3.4 3- and 4-(Difluoromethyl)pyrrolidines

4 (Monofluoroalkyl)pyrrolidines

4.1 2-(Monofluoromethyl)pyrrolidines

4.2 2-(Monofluoroalkyl)pyrrolidines

4.3 2-(Monofluoroalkenyl)pyrrolidines

5 Conclusion

中文翻译：

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氟吡咯烷和（氟烷基）吡咯烷的合成

感谢Kene Uneyama教授和Donald J. Burton教授对氟有机化学的巨大贡献

抽象的

吡咯烷及其衍生物在药物化学和有机合成中非常重要。氟吡咯烷和（氟烷基）吡咯烷已被用于制备药物以及还用作有机催化剂。通过吡咯烷衍生物的氟化或通过已经包含氟代烷基前体的多步合成来实现此类化合物的合成。

1引言

1.1含氟吡咯烷酮的一般利益

1.2 Fluoroalkylpyrrolidines和Gauche的影响

2氟吡咯烷

2.1 3-氟吡咯烷

2.2 3,3-和3,4-二氟吡咯烷

2.3 3,3,4-三氟吡咯烷

2.4 3,3,4,4-四氟吡咯烷

3（二氟甲基）-和（三氟甲基）吡咯烷

3.1 2-（三氟甲基）吡咯烷

3.2 3-和4-（三氟甲基）吡咯烷

3.3 2-（二氟甲基）吡咯烷

3.4 3-和4-（二氟甲基）吡咯烷

4（一氟烷基）吡咯烷

4.1 2-（单氟甲基）吡咯烷

4.2 2-（单氟烷基）吡咯烷

4.3 2-（单氟烯基）吡咯烷

5结论

吡咯烷及其衍生物在药物化学和有机合成中非常重要。氟吡咯烷和（氟烷基）吡咯烷已被用于制备药物以及还用作有机催化剂。通过吡咯烷衍生物的氟化或通过已经包含氟代烷基前体的多步合成来实现此类化合物的合成。

1引言

1.1含氟吡咯烷酮的一般利益

1.2 Fluoroalkylpyrrolidines和Gauche的影响

2氟吡咯烷

2.1 3-氟吡咯烷

2.2 3,3-和3,4-二氟吡咯烷

2.3 3,3,4-三氟吡咯烷

2.4 3,3,4,4-四氟吡咯烷

3（二氟甲基）-和（三氟甲基）吡咯烷

3.1 2-（三氟甲基）吡咯烷

3.2 3-和4-（三氟甲基）吡咯烷

3.3 2-（二氟甲基）吡咯烷

3.4 3-和4-（二氟甲基）吡咯烷

4（一氟烷基）吡咯烷

4.1 2-（单氟甲基）吡咯烷

4.2 2-（单氟烷基）吡咯烷

4.3 2-（单氟烯基）吡咯烷

5结论