Trifluoromethylated pyranose derivatives as the chiral dopant for ferroelectric liquid crystals

Itoh, K.; Takeda, Mayu; Namekawa, Masaaki; Nayuki, Shinichi; Murayama, Yoshinobu; Yamazaki, Takashi; Kitazume, Tomoya

doi:10.1080/00150199308019934

Cited by 21 publications

(1 citation statement)

References 14 publications

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“…These special properties of fluorine have been exploited for the development of new and effective biochemical tools as well as agrochemical, medicinal, and therapeutic agents, particularly in the field of enzymatic inhibition . Particularly attractive are 2,2-difluoro-3-hydroxyacids, which are versatile intermediates for the preparation of a variety of bioactive materials, such as difluorinated gingerol, a potent inhibitor of prostaglandin biosynthesis, chiral 2,2-difluorocitrate as inhibitors of rat liver ATP citrate lyase and porcine heart aconitase or yeast mitochondria, difluorostatine peptides as potent and specific renin inhibitors, proteolysis inhibitors or ferroelectric liquid crystals, among others. Although a number of procedures have been developed to prepare 2,2-difluoro-3-hydroxyacids, , new, efficient methods of preparation from cheap, easily available fluorinated materials are always desirable.…”

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A New, Mild, and Efficient Synthesis of 2,2-Difluoro-3-hydroxyacids through a Selective Haloform Reaction

2005

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[reaction: see text] Long-chain 2,2-difluoro-3-hydroxyacids have been synthesized in a new, straightforward manner by treatment of 4-hydroxy-1,1,1,3,3-pentafluoroalkyl ketones, easily obtained by reaction of pentafluoroenolate 2 with aldehydes and ketones, with base under mild conditions. The reaction sequence is marked by the selective cleavage of the CO-CF3 bond, as well as the absence of products arising from the alternative CO-CF2R bond cleavage. The process represents a convenient approach for the synthesis of 2,2-difluoro-3-hydroxyacids, as it is short, provides good to excellent yields under mild conditions, and uses hexafluoro-2-propanol, a very cheap reagent, as the fluorine source.

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