108535-33-7Relevant academic research and scientific papers
Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media
Hamada, Hiroki,Shiromoto, Mizuho,Funahashi, Makoto,Itoh, Toshiyuki,Nakamura, Kaoru
, p. 2332 - 2336 (2007/10/03)
Lipase-catalyzed esterification was successfully utilized for the optical resolution of 1,1,1-trifluoro-2-alkanol 1 when racemic 1 was treated with lipase from Candida antarctica in hexane in the presence of molecular sieves (4 A) to provide the corresponding (S)-acetate 2 in an optically pure state. Alkanol 1 is known as an important component of liquid crystal compounds which display remarkable ferroelectric liquid crystal (FLC) characteristics. Five types of optically pure alkanols, i.e., 1,1,1-trifluoro-2-octanol (1a), 1,1,1-trifluoro-2-nonanol (1b), 1,1,1-trifluoro-2-decanol (1c), 1,1,1-trifluoro-2-undecanol (1d), and 1,1,1-trifluoro-8-(benzyloxy)-2-octanol (1e), were thus obtained by the lipase-catalyzed acylation.
Chiral Synthesis Via Organoboranes. 38 Selective Reductions. 48. Asymmetric Reduction of Trifluoromethyl Ketones by B-Chlorodiisopinocampheylborane in High Enantiomeric Purity
Ramachandran, P. Veeraraghavan,Teodorovic, Aleksandar V.,Brown, Herbert C.
, p. 1725 - 1738 (2007/10/02)
(-)-B-Chlorodiisopinocampheylborane TM,1>, introduced by us several years ago, has been shown to reduce prochiral aryl and alkyl perfluorinated ketones to the corresponding optically active alcohols in very high ee.For example, 2,2,2-trifluoroacetophenone, trifluoroacetyl-1-naphthalene, and trifluoroacetyl-2-naphthalene are all reduced with 1 within 1-3 d at rt in 90percent ee, 78percent ee and 91percent ee, respectively.The optical purity of 1-phenyl-2,2,2-trifluoroethanol is upgraded to = 99percent ee by crystallizing the initially formed products from pentane. 1,1,2,2,2- pentafluoropropiophenone and 1,1,2,2,3,3,3-heptafluorobutyrophenone are reduced in 3 d with 1 to the corresponding alcohols in 92percent ee and 87 percent ee, respectively.The reagent reduces alkyl trifluoromethyl ketones at a rate faster than that of the aryl derivatives, while still providing the product alcohols in very high ee.Thus, 1,1,1-trifluoroacetone, 1,1,1-trifluorononan-2-one, and 1,1,1-trifluorodecan-2-one are all reduced within 4 - 8 h in 89percent ee, 92percent ee, and 91percent ee, respectively.Even α-sec-alkyl trifluoromethyl ketones are handled by 1 very efficiently.Thus cyclohexyl trifluoromethyl ketone is reduced by 1 at rt in 12 h to the product alcohol in 87percent ee.In all of these cases the trifluoromethyl group acts as the enantiocontrolling larger group as compared to the aryl or alkyl group.This produces alcohol products with stereochemistry opposite to those obtained for the corresponding hydrogen analogs.The steric and electronic influence of the trifluoromethyl group in achieving enantiocontrol in assymmetric reductions is discussed.Keywords: asymmetric reduction; trifluoromethyl ketones; DIP-Chloride; high enantiomeric purity
Stereoselective Synthesis of Fluorinated Materials Catalyzed by an Antibody
Kitazume, Tomoya,Lin, Jenq Tain,Takeda, Mitsunori,Yamazaki, Takashi
, p. 2123 - 2126 (2007/10/02)
A monoclonal antibody, elicited by a transition-state analogue for the hydrolysis of fluorinated esters, acted as an enzymelike catalyst for the preparation of chiral fluorinated compounds. The syntheses of (R)- or (S)-1-(fluoroalkyl)alkanols and an allyl
TRIFLUOROPROPENE OXIDE AS A TRIFLUOROMETHYL SOURCE. PREPARATION OF OPTICALLY ACTIVE ALCOHOLS
Takahashi, Osamu,Furuhashi, Keizo,Fukumasa, Mitsuo,Hirai, Toshihiro
, p. 7031 - 7034 (2007/10/02)
Optically active 3,3,3-trifluoropropene oxide (TFPO) was converted to 1,1,1-trifluoro-2-ols via Grignard type or Friedel-Crafts type reaction.The regio-selectivity of the latter reaction was discussed through an MO calculation.
SYNTHETIC APPROACH TO STEREOISOMERS OF ALLYLIC ALCOHOLS POSSESING A TRIFLUOROMETHYL GROUP
Kitazume, Tomoya,Lin, Jeng Tain,Yamazaki, Takashi,Takeda, Mitsunori
, p. 177 - 188 (2007/10/02)
A number of stereoisomers of optically pure allylic alcohols with a trifluoromethyl group were prepared, utilizing the enantiotopic specifity of assymetric hydrolysis of their acetates by hydrolyses.Their absolute configurat
A Microbially Based Approach for the Preparation of Chiral Molecules Possessing the Trifluoromethyl Group
Lin, Jenq Tain,Yamazaki, Takashi,Kitazume, Tomoya
, p. 3211 - 3217 (2007/10/02)
The synthetic approach to both enantiomers and diastereomers with the trifluoromethyl group, involving the stereoselective hydrolysis of the ester group and acyclic stereoselection, is described.The absolute configuration of these trifluoromethylated mole
