Regio‐ and Stereoselective Synthesis of Vicinal Fluorohydrins

Abstract

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Fluorinated Isatin Derivatives. Part 2. New N-Substituted 5-Pyrrolidinylsulfonyl Isatins as Potential Tools for Molecular Imaging of Caspases in Apoptosis

“…In recent years, fluorohydrins , have attracted much attention in organofluorine chemistry as they act as precursors in the synthesis of biochemically active, monofluorinated analogues of natural products , such as steroids, amino acids, and carbohydrates. − One of the main reasons for unique biological properties of vicinal fluorohydrins could be attributed to the fact that the presence of fluorine at vicinal position to the free hydroxyl group increases the acidity of hydroxyl function and hence influences its ability to act as hydrogen bond donor and/or acceptor. So, when biochemically active fluorohydrins are administered into the body, they may show enhanced activity against their in vivo targets (enzymes/receptors) compared to their nonfluorinated counterparts due to modified cell permeability and biodistribution. − …”

“…Synthesis of Fluorohydrins from Epoxides. In recent years, fluorohydrins 40,54 have attracted much attention in organofluorine chemistry 55 as they act as precursors in the synthesis of biochemically active, monofluorinated analogues of natural products 56,57 such as steroids, 58 amino acids, 59 and carbohydrates. [60][61][62] One of the main reasons for unique biological properties of vicinal fluorohydrins could be attributed to the fact that the presence of fluorine at vicinal position to the free hydroxyl group increases the acidity of hydroxyl function and hence influences its ability to act as hydrogen bond donor and/ or acceptor.…”

Monofluorination of Organic Compounds: 10 Years of Innovation

“…The past ten years have been filled with novel synthetic pathways for the formation of β-fluoroalcohols, ethers or esters using either nucleophilic or electrophilic sources of fluorine atoms . β-Fluorohydrin derivatives and fluorinated oxygen-containing cycles have been given special interest because of their presence in a variety of biologically active compounds …”

Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling

“…Enantiomerically pure β 2 - and β 2,2 -amino ketones are prevalent in biologically active compounds 28 and are direct precursors 29 – 32 to a number of important chiral structural motifs such as β 2 - and β 2,2 -amino acids, derivatives for peptide synthesis 30 , 31 , and fluorohydrins 32 . For example, the treatment of β 2,2 -amino ketone 6j with N , N ʹ, N ʺ-trichloroisocyanuric acid ( 9 ), followed by p -toluenesulfonyl chloride could replace the para -methoxyphenyl (PMB) N -protective group with a tosyl (Ts) group (Fig.…”