| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344499 | Tetrahedron: Asymmetry | 2011 | 6 Pages |
A concise synthesis of enantiopure (S)- and (R)-α-Tfm-aspartic acid and α-Tfm-serine is reported. The key step involves a Strecker-type reaction on chiral CF3-oxazolidines (Fox) derived from ethyl 4,4,4-trifluoroacetoacetate (ETFAA) or ethyl trifluoropyruvate.
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(3S,5R)-3-Carboethoxymethyl-3-trifluoromethyl-5-phenylmorpholin-2-oneC15H16F3NO4[α]D21=+55.3 (c 1.3, CH2Cl2)Source of chirality: (R)-phenylglycinolAbsolute configuration: (3S,5R)
(3R,5R)-3-Carboethoxymethyl-3-trifluoromethyl-5-phenylmorpholin-2-oneC15H16F3NO4[α]D21=-24 (c 0.5, CHCl3)Source of chirality: (R)-phenylglycinolAbsolute configuration: (3R,5R)
(S)-α-Trifluoromethylaspartic acid hydrochlorideC5H7ClF3NO4[α]D21=+25 (c 0.25, H2O)Source of chirality: (R)-phenylglycinol and asymmetric synthesisAbsolute configuration: (S)
(S)-2-Trifluoro-3-hydroxy-2-[(1R)-2-hydroxy-1-phenyl-amino]propanenitrileC12H13F3N2O2[α]D21=-77.4 (c 1.0, CHCl3)Source of chirality: (R)-phenylglycinolAbsolute configuration: (S,R)
(R)-2-Trifluoro-3-hydroxy-2-[(1R)-2-hydroxy-1-phenyl-amino]propanenitrileC12H13F3N2O2[α]D21=-83.3 (c 1.0, CHCl3)Source of chirality: (R)-phenylglycinolAbsolute configuration: (R,R)
(R)-α-TrifluoromethylserineC4H6F3NO3[α]D23=+10.6 (c 1, H2O)Source of chirality: (R)-phenylglycinol and asymmetric synthesisAbsolute configuration: (R)
