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- Title
New Synthesis and Chirality of (−)-4,4,4,4′,4′,4′-Hexafluorovaline.
- Authors
Eberle, Marcel K.; Keese, Reinhart; Stoeckli-Evans, Helen
- Abstract
(−)-( R)-4,4,4,4′,4′,4′-Hexafluorovaline hydrochloride (( R)- 5) of 98% ee is prepared from β,β-bis(trifluoromethyl)acrylic acid (= benzyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate; 1) in 4 steps with an overall yield of 9.6%. Key step is the separation of the TsOH salts of the diastereoisomers obtained by anti-Michael addition of (+)-( R)-1-phenylethylamine ( 2) to 1 (→ ( R,R)- 3). In contrast to the published ( S)-chirality, the X-ray structure analysis of ( R, S)- 6 reveals, that ( R)-chirality has to be assigned to the levorotatory (−)-4,4,4,4′,4′,4′-hexafluorovaline hydrochloride.
- Publication
Helvetica Chimica Acta, 1998, Vol 81, Issue 1, p182
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19980810117