Journal ArticleDOI
General method for the synthesis of enantiomerically pure β-hydroxy-α-amino acids, containing fluorine atoms in the side chains. Case of stereochemical distinction between methyl and trifluoromethyl groups. X-Ray crystal and molecular structure of the nickel(II) complex of (2S,3S)-2(trifluoromethyl)threonine
Vadim A. Soloshonok,V. P. Kukhar,Sergei V. Galushko,Nataly Yu. Svistunova,Dimitri V. Avilov,Nadia A. Kuz'mina,Nicolai I. Raevski,Yuri T. Struchkov,Alexander P. Pysarevsky,Yuri N. Belokon +9 more
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TLDR
In this article, the chiral NiII complex 1 of a Schiff's base derived from (S)-o-[N-(benzylprolyl)amino] benzophenone (BPB) and glycine was treated with fluoro-substituted aldehydes (aliphatic and aromatic) in MeOH or CHCl3.Abstract:
The chiral NiII complex 1 of a Schiff's base derived from (S)-o-[N-(N-benzylprolyl)amino] benzophenone (BPB) and glycine was treated with fluoro-substituted aldehydes (aliphatic and aromatic)in MeOH or CHCl3. The addition proceeds with high diastereoselectivity to give, if catalysed by MeONa in MeOH, the corresponding complexes of syn-(2R)-3-fluorophenylserines (84–100% d.e.) and syn-(2S)-fluoroalkylserines (90% d.e.), and, if catalysed by NEt3 or DABCO (MeOH or CHCl3), the corresponding complexes of syn-(2S)-, and anti-(2S)-3-fluorophenylserines and fluoroalkylserines. The second-order asymmetric transformation may be successfully employed to obtain diastereoisomerically pure complexes of anti-(2R)-3-fluorophenylserines. Condensation of trifluoroacetone with complex 1, catalysed by MeONa, gave predominantly (at least >95% d.e.) the diastereoisomeric complex, containing (2S,3S)-β-(trifluoromethyl)threonine, as shown by an X-ray diffraction structural study. Diastereoisomerically and enantiomerically pure fluorine-containing 3-phenyl- and 3-alkyl-serines were obtained from the corresponding diastereoisomerically pure complexes, separated by chromatography or crystallization. The initial chiral auxiliary BPS was recovered (80–98%). The influence of the reaction's conditions and the nature of the corresponding fluoro-substituted aldehydes on the diastereoselectivity of the reactions is discussed.read more
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Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.
TL;DR: In this Perspective, applications of fluorine in the construction of bioisosteric elements designed to enhance the in vitro and in vivo properties of a molecule are summarized.
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Remarkable Amplification of the Self‐Disproportionation of Enantiomers on Achiral‐Phase Chromatography Columns
Journal ArticleDOI
Phenomenon of optical self-purification of chiral non-racemic compounds
Vadim A. Soloshonok,Hisanori Ueki,Manabu Yasumoto,Shekar Mekala,Jennifer S. Hirschi,Daniel A. Singleton +5 more
TL;DR: The phenomenon of optical self-purification reported here deserves further systematic study as possibly one of the mechanisms leading to the emergence and maintenance of prebiotic homochirality.
Journal ArticleDOI
Crystallization-induced diastereomer transformations
Journal ArticleDOI
Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group
TL;DR: In this article, a review article provides a critical overview of several different synthetic approaches developed for asymmetric preparation of fluorine-containing amines, amino alcohols, α- and β-amino acids.
References
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Synthesis of optically active α-amino acids
TL;DR: Asymmetric derivatization of glycine as mentioned in this paper has been shown to be a useful technique for the synthesis of complex amino acids. But it is difficult to verify its correctness.
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Organic Synthesis—Where now?
TL;DR: For a review of the major developments in organic synthesis during the past 25 years, and to project them into the future, see, e.g., the authors, for instance, the authors of this article.
Journal ArticleDOI
Suicide substrates: mechanism-based enzyme inactivators
TL;DR: Suicide substrates are defined as a class of irreversible inactivators of specific target enzymes where the target enzyme participates in its own destruction by catalytic unmasking of a latent functional group at some stage in the catalytic cycle of the enzyme.