Special articles on synthesis and supramolecular structure of functionality amphiphiles. Synthesis and properties of ferroelectric liquid crystals with trifluoromethyl group at a chiral center.

Efficient Synthesis of Optically Pure 1,1,1-Trifluoro-2-alkanols through Lipase-Catalyzed Acylation in Organic Media

“…The racemic 1,1,1-trifluoroalkanols were prepared as shown in Scheme . Initially, we prepared trifluoromethyl ketones 2 by a known method 2d. The substitution reaction of the magnesium bromide salt of trifluoroacetic acid (TFA) with a Grignard reagent was attempted; however, the reaction provided 2 in poor chemical yield (20−30%), and also required an excess amount of the reagent.…”

“…A recent study revealed that chiral FLC compounds, which involve optically active 1,1,1-trifluoroalkanols 1 , possess remarkable characteristics such as a wide temperature range of the Sc* phase, a large spontaneous polarization, and a short response time (Figure ) 1c. Only three preparation methods have been reported for optically active 1 . The first example is optical resolution through the lipase-catalyzed hydrolysis of the corresponding racemic esters, though high enantioselection was allowed for a limited number of compounds 2a.…”

“…Only three preparation methods have been reported for optically active 1 . The first example is optical resolution through the lipase-catalyzed hydrolysis of the corresponding racemic esters, though high enantioselection was allowed for a limited number of compounds 2a. The second example is the enantioselective reduction of trifluoromethyl ketones by bakers' yeast,2b or plant tissue cultures from Nicotiana tabacum which we recently reported 2c.…”

“…The first example is optical resolution through the lipase-catalyzed hydrolysis of the corresponding racemic esters, though high enantioselection was allowed for a limited number of compounds 2a. The second example is the enantioselective reduction of trifluoromethyl ketones by bakers' yeast,2b or plant tissue cultures from Nicotiana tabacum which we recently reported 2c. The third method is the classical resolution of racemic 1 as diastereomeric esters using optically pure trans -2-benzamidocyclohexanoic acid 2d…”

“…The second example is the enantioselective reduction of trifluoromethyl ketones by bakers' yeast,2b or plant tissue cultures from Nicotiana tabacum which we recently reported 2c. The third method is the classical resolution of racemic 1 as diastereomeric esters using optically pure trans -2-benzamidocyclohexanoic acid 2d 1 Model structure of ferroelectric liquid crystals 1c…”