Diethylaminosulfur Trifluoride (DAST) Mediated Transformations Leading to Valuable Building Blocks and Bioactive Compounds

Abstract

Nucleophilic fluorination is one of the fundamental reactions in organic chemistry, as well as a convenient tool for the synthesis of fluorinated building blocks with a potential biological activity. In this minireview, diethylaminosulfur trifluoride (DAST) mediated reactions leading to valuable building blocks and bioactive compounds will be discussed. We focused on results that have been published since 2010. Transformation of βamino alcohols, heterocyclic frameworks synthesis, as well as rearrangement reactions have been described in detail.

Deoxyfluorinating reagents as tools for γ-amino-α-hydroxyphosphonate modification

“…1 H NMR, 13 C NMR, 19 F NMR, 31 P NMR and 2D spectra were obtained on a Bruker ASCEND 400 (400 MHz) or Bruker ASCEND 600 (600 MHz) spectrometer. Chemical shifts in the…”

“…In some cases, such reactions result in cyclization, rearrangement or etherification transformations, or even provide products without a fluorine atom. 19 The main objective of this work was further extension of our previous studies on the regioselective fluorination of α-hydroxy-β-aminophosphonates (Scheme 1) and application of the resulting compounds as potential tools in the synthesis of their dipeptide analogues. [20][21][22][23][24] In this paper, we would like to present some transformations of α-hydroxyγ-aminophosphonates which took place in reactions with DAST and PyFluor (Scheme 1).…”

Diversity-Oriented Synthesis Catalyzed by DAST – Preparation of New Antitumor Ecdysteroid Derivatives

“…Diethylaminosulfur trifluoride (DAST) is a mild, nucleophilic reagent that may convert non-phenolic alcohols, aldehydes and ketones, carboxylic acids, and sulfoxides into monofluorides, difluorides, acyl fluorides and α-fluoro sulfides, respectively. Other than fluorination, however, DAST is known to catalyze the formation of many further building blocks valuable for medicinal chemistry, including various heterocycles through dehydration and intramolecular cyclization [4], sulfonamides through cross-coupling of arylboronic acids [5], aromatic thiols [6], etc. Previously, we reported the DAST catalyzed transformation of 20-hydroxyecdysone 2,3;20,22-diacetonide, and obtained 14-and/or 25fluorinated, and Δ 14,15 analogs with or without a 25-fluorine moiety [7].…”

Diversity-Oriented Synthesis Catalyzed by Diethylaminosulfur-Trifluoride—Preparation of New Antitumor Ecdysteroid Derivatives

“…Diethylaminosulfur trifluoride (DAST) is a mild, nucleophilic reagent that may convert non-phenolic alcohols, aldehydes and ketones, carboxylic acids, and sulfoxides into monofluorides, difluorides, acyl fluorides, and α-fluoro sulfides, respectively. Other than fluorination, however, DAST is known to catalyze the formation of many further building blocks valuable for medicinal chemistry, including various heterocycles through dehydration and intramolecular cyclization [ 6 ], sulfonamides through cross-coupling of arylboronic acids [ 7 ], aromatic thiols [ 8 ], etc. Previously, we reported the DAST catalyzed transformation of 20-hydroxyecdysone 2,3;20,22-diacetonide, and obtained 14- and/or 25-fluorinated and Δ 14,15 analogs with or without a 25-fluorine moiety [ 9 ].…”