Recent Progress in the Selective Fluorinations of Some Functionalized Cycloalkenes

Abstract

Organofluorine compounds have had an increasing impact in synthetic organic chemistry and pharmaceutical research over the past two decades. Their syntheses and the development of novel synthetic approaches towards versatile fluorinated small molecules have received great interest. Our research team has designed various selective and stereocontrolled methods for the construction of fluorine‐containing small molecular entities, involving the transformation of various functionalized cycloalkenes across their ring olefin bond. The synthetic methodologies developed to access various pharmacologically interesting fluorinated derivatives with multiple chiral centers might be valuable protocols for the preparation of other classes of organic compounds as well.

Application of Metathesis Protocols to the Stereocontrolled Synthesis of some Functionalized β‐Amino Esters and Azaheterocycles

“…As a consequence of the high relevance of cyclic β-amino acid derivatives, transformation and preparation of such compounds was a highlighted topic, and many synthetic routes were developed. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] In this chapter, after a brief introduction to olefin metathesis, those synthetic pathways will be discussed whose key steps were ring-opening and cross-metathesis. [29][30][31][32][33]…”

“…Such molecular entities can be found in a large number of natural products, bioactive compounds, and drugs [1–19] . A wide variety of methods were developed during last two decades to obtain such derivatives [20–33] . Azaheterocyclic β‐amino acid derivatives were also synthesized through oxidative ring opening followed by cyclization across double reductive amination [26,30–36] …”

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] A wide variety of methods were developed during last two decades to obtain such derivatives. [20][21][22][23][24][25][26][27][28][29][30][31][32][33] Azaheterocyclic β-amino acid derivatives were also synthesized through oxidative ring opening followed by cyclization across double reductive amination. [26,[30][31][32][33][34][35][36] Highly functionalized azaheterocycles (including the azaheterocyclic β-amino acid derivatives) are an interesting and highly abundant compound class in pharmaceutical and medicinal chemistry.…”

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

“…But, with 2′-F-ribonucleoside, there was no such kind of interactions and fluorine hydrogen bond (Fig. 3b) (Caron 2020;Nonn et al 2022).…”

“…Traditionally, we introduce fluorine atom/s by electrophilic or nucleophilic reagents and a good number of reagents have been developed (Caron 2020). In the last ten years, a growth of interest has been seen in the development of methods of fluorination through thermal (Nonn et al 2022;Dong and Tsui 2021;Campbell and Ritter 2014) or photochemical radical reactions (Sibi and Landais 2013;Kindt and Heinrich 2014;Li et al 2013;Cui et al 2016;Meyer et al 2018). We have now good methods of regio-and enantioselective introduction of a fluorine atom or fluorine-containing substituent in organic compounds.…”