95853-80-8Relevant articles and documents
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).