114717-14-5Relevant articles and documents
Synthesis of novel non-proteinogenic α-amino acids with charged imidazolium fragment in the side chain
Maleev,Grachev,Khrustalev,Dolgushin
experimental part, p. 1273 - 1283 (2011/02/23)
Zwitterionic imidazolium and benzimidazolium salts bearing chiral amino acid moiety were synthesized using chiral NiII complexes. Different N-derivatives of the synthesized enantiomerically pure amino acids were prepared; their zwitterionic str
Synthesis of novel chiral NiII complexes of dehydroalanine Schiff bases and their reactivity in asymmetric nucleophilic addition reactions. Novel synthesis of (S)-2-carboxypiperazine
Saghiyan, Ashot S.,Stepanyan, Lala A.,Manasyan, Luiza L.,Geolchanyan, Arpine V.,Djamgaryan, Silva M.,Ajvazyan, Hrant R.,Panosyan, Henry A.,Maleev, Viktor I.,Saveleva, Tatiana F.
scheme or table, p. 2638 - 2645 (2011/02/16)
New chiral NiII complexes of Schiff bases of dehydroalanine with modified chiral auxiliaries (S)-2-N-[N′-(3,4-dichlorobenzyl)prolyl] aminobenzophenone (3,4-DCBPB), (S)-2-N-[N′-(3,4-dimethylbenzyl)prolyl] aminobenzophenone (3,4-DMBPB), (S)-2-N-[N′-(2-chlorobenzyl)prolyl] aminobenzophenone (2-CBPB), and (S)-2-N-[N′-(2-fluorobenzyl)prolyl]- aminobenzophenone (2-FBPB) have been synthesized. Asymmetric Michael addition reactions of primary and secondary amines and thiols to the dehydroalanine moieties of the complexes were studied. (S)-2-FBPB was found to be the best chiral auxiliary in terms of both selectivity of the reactions (de ～92-96%) and reactivity of the complexes. A novel synthetic route toward (S)-2-carboxypiperazine was developed based on the auxiliary.
ASYMMERTIC SYNTHESIS OF Β-SUBSTITUTED α-AMINO ACIDS VIA A CHIRAL Ni(II) COMPLEX OF DEHYDROALANINE
Belokon, , Yuri N.,Sagyan, Ashot S.,Djamgaryan, Silva M.,Bakhmutov, Vladimir I.,Belikov, Vasili M.
, p. 5507 - 5514 (2007/10/02)
An efficient approach to the asymmetric synthesis of β-substituted (S)-alanines is describen.The chiral Ni(II) complex of a Schiff base derived from (S)-o-N-(N-benzylpropyl)aminobenzophenone (BBP) and glycine was treated with formaldehyde and sodium methoxide to give a corresponding (R)-serine complex which, in turn, was converted to the chiral Ni(II) dehydroalanine complex.Michael type base catalyzed addition of nucleophiles (including MeOH, Me2NH, PhCH2NH2, imidazole, PhSH, PhCH2SH,, malonic ester and benzylmagnesium chloride) produced a mixture of diastereoisomeric complexes with a 70-90percent excess of S,S (or L,L) isomers over the S,R (or L,D) ones.The cleavage of pure diastereoisomers with aqueous HCl gave, in good yields, β-substituted (S) (or L)-alanines and regenerated the chiral auxiliary (BBP).
