600-21-5Relevant articles and documents
Sporidesmins. 8. Ovine ill-thrift in Nova Scotia. 3. The characterisation of chetomin a toxic metabolite of Chaetomium cochliodes and Chaetomium globosum.
Safe,Taylor
, p. 472 - 479 (1972)
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Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies
Dzygiel, Pawel,Reeve, Toby B.,Piarulli, Umberto,Krupicka, Martin,Tvaroska, Igor,Gennari, Cesare
supporting information; experimental part, p. 1253 - 1264 (2009/04/07)
The efficient resolution of racemic N-benzyl α-amino acids (N-Bn-AA) has been achieved by a liquid-liquid extraction process using the lipophilic chiral salen-cobalt(III) complex [CoIII(3)(OAc)]. As a result of the resolution by extraction, one enantiomer (S) of the N-benzyl α-amino acid predominated in the aqueous phase, while the other enantiomer (R) was driven into the organic phase by complexation to cobalt. The complexed amino acid (R) was then quantitatively released by a reductive (CoIII→Co II) counter-extraction with aqueous sodium dithionite or L-ascorbic acid in methanol. The reductive cleavage allowed to recover the [Co II(3)] complex in good yield, which could be easily re-oxidized to [CoIII(3)(OAc)] with air/AcOH and reused with essentially no loss of reactivity and selectivity. Investigation on the nitrogen substitution indicates that the presence of a single benzyl group on the amino acid nitrogen is important to obtain high enantioselectivity in the extraction process. The kinetic vs. thermodynamic nature of the resolution process was also investigated with an enantiomeric exchange experiment, which shows that the liquid-liquid extraction with [CoIII(3)-(OAc)] is an equilibrium process operating under thermodynamic control. In the absence of a suitable crystal structure of the [CoIII(3)(N-Bn-AA)] complexes, computational and spectroscopic studies were used to investigate how the N-benzyl α-amino acids are accommodated in the "binding pocket" of the chiral cobalt complex. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis and utilization of a novel glycine derived chiral precursor, based on a recyclable L-prolinol auxiliary, for the enantioselective preparation of α-amino acids and their N-methyl derivatives
Pandey,Reddy,Das
, p. 3175 - 3178 (2007/10/03)
α-Amino acids and their N-methyl derivatives are synthesized in fairly high optical purity employing a new glycine derived template based on a recyclable L-prolinol chiral auxiliary.
