Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence

Abstract

A study exploring the chemical behavior of some dihydroxylated β-amino ester stereo- and regioisomers, derived from unsaturated cyclic β-amino acids is described. The nucleophilic fluorinations involving hydroxy–fluorine exchange of some highly functionalized alicyclic diol derivatives have been carried out in view of selective fluorination, investigating substrate dependence, neighboring group assistance and chemodifferentiation.

Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

“…Another method is based on the application of fluorine-containing building blocks such as fluorinated amines. [20][21][22][23][24][25][26] The synthesis of various types of fluorinated functionalized azaheterocycles based on oxidative ring opening of some substituted alkenes followed by cyclization with reductive amination has been reported in recent years. [24][25][26] Further extension and improvement of the above stereocontrolled procedure to the access of novel fluorine-containing saturated N-heterocycles has been extensively investigated.…”

“…[20][21][22][23][24][25][26] The synthesis of various types of fluorinated functionalized azaheterocycles based on oxidative ring opening of some substituted alkenes followed by cyclization with reductive amination has been reported in recent years. [24][25][26] Further extension and improvement of the above stereocontrolled procedure to the access of novel fluorine-containing saturated N-heterocycles has been extensively investigated. The key step of the synthetic procedure is the reductive amination of dialdehydes using primary alkylamines or primary fluorinated amines.…”

Synthesis of complex unnatural fluorine-containing amino acids

“…Cyclopentane-containing amino acids are another class of compounds which have seen increasing interest [ 118 , 119 ]. They are particularly beneficial as they can be introduced in the place of proline to alter physical and chemical properties of compounds.…”

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

“…There are already many drugs on the market, which contain at least one fluorine atom, and this number is expected to increase in years to come. [15][16][17] Application of fluorinated compounds like fluorine-containing amines could offer a route to the access of fluorine-containing azaheterocycles.…”

“…Taking into consideration of the high biorelevance of saturated N-heterocycles [1][2][3][4][5][6][7][8][9] and organofluorine molecules, [15][16][17] the combination of these molecular structures is a hot topic in synthetic and medicinal chemistry. The synthetic methods…”