Journal of Organic Chemistry p. 4511 - 4522 (1989)
Update date:2022-08-04
Topics:
Ojima, Iwao
Kato, Koji
Nakahashi, Kazuaki
Fuchikami, Takamasa
Fujita, Makoto
New and efficient syntheses of 4,4,4-trifluorovaline (1), 5,5,5-trifluoronorvaline (2), 5,5,5-trifluoroleucine (5), 6,6,6-trifluoronorleucine (6), 4,5,6,7-tetrafluorotryptophan (25), and α-(trifluoromethyl)-β-alanine are studied.Trifluorovaline (1) and trifluoronorvaline (2) are synthesized through amidocarbonylation of 2-(trifluoromethyl)propanal (2-TFMPA) and 3-(trifluoromethyl)propanal (3-TFMPA), respectively, followed by hydrolysis.Trifluoroleucine (5) and trifluoronorleucine (6) are synthesized by using modified Erlenmeyer's azlactone method from 2-TFMPA and 3-TFMPA, respectively. (S)- and (R)-trifluoronorvalines <(S)-2 and (R)-2> and trifluoronorleucines <(S)-6 and (R)-6> with high enantiomeric purities (95-100percent ee) are obtained through enzymatic optical resolution of N-acetyltrifluoronorvaline (4) and N-acetyltrifluoronorleucine (17) with the use of a porcine kidney acylase I.Optically active trifluoronorleucine <(S)-6, 87-89percent ee> is also obtained via the asymmetric hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (10a-Z) with a chiral rhodium catalyst,
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