6975-13-9Relevant academic research and scientific papers
Diastereoselectivity of enolate anion protonation. H/D exchange of β-substituted ethyl butanoates in ethanol-d
Mohrig, Jerry R.,Rosenberg, Robert E.,Apostol, John W.,Bastienaansen, Mark,Evans, Jordan W.,Franklin, Sonya J.,Frisbie, C. Daniel,Fu, Sabrina S.,Hamm, Michelle L.,Hirose, Christopher B.,Hunstad, David A.,James, Thomas L.,King, Randall W.,Larson, Christopher J.,Latham, Hallie A.,Owen, David A.,Stein, Karin A.,Warnet, Ronald
, p. 479 - 486 (2007/10/03)
The stereochemistry of base-catalyzed H/D exchange on 13 β-substituted ethyl butanoates in ethanol-d has been studied in order to analyze the steric and electronic factors which control the diastereoselectivity of electrophilic attack on enolate anions. E
Nonproteinogenic Amino Acids, II. - Synthesis and Determination of the Absolute Configuration of (2S,4S)-(-)- and (2S,4R)-(+)-5,5,5-Trifluoroleucine
Weinges, Klaus,Kromm, Erich
, p. 90 - 102 (2007/10/02)
The synthesis (Scheme 1) of racemic 4,4,4-trifluoro-3-methyl-1-butanol (5) and the resolution of its enantiomers is described.The absolute configuration of the negatively rotating enantiomer of 5 is correlated to that of the optically active fermentation amyl alcohol (S-10) via (S)-(-)-1,1,1-trifluoro-2-methylbutane (S-8) (Scheme 2).Oxidation of optically pure (R)-(+)-4,4,4-trifluoro-3-methyl-1-butanol (R-5) yields the aldehyde R-6 which is employed as starting material for the asymmetric Strecker synthesis of (2S,4R)-(+)-5,5,5-trifluoroleucine (13a).The analogous synthesis with (+/-)-4,4,4-trifluoro-3-methyl-1-butanol (6) via the aminonitrile 11 affords the optically pure (2S,4S)-diastereoisomer 11b which leads to enantiomerically pure (2S,4S)-(-)-5,5,5-trifluoroleucine (13b).
ASYMMETRICAL REDUCTION OF PERFLUOROALKYLATED KETONES, KETOESTERS AND VINYL COMPOUNDS WITH BAKER'S YEAST
Kitazume, Tomoya,Ishikawa, Nobuo
, p. 237 - 238 (2007/10/02)
Reduction of perfluoroalkylated ketones, ketoesters and vinyl compounds with baker's yeast was studied.The ketones and β-ketoesters were asymmetrically reduced to give optically active perfluoroalkylated carbinols and hydroxyesters, while the vinyl compounds were reduced to perfluoroalkylated alkanes.
