Asymmetric synthesis of enantiomerically enriched (S)-¦Á-aminopropionic acids containing heterocyclic side chains

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• 作者：Ashot S. Saghyan^a ; ^b ; ^{sagysu@netsys.am} ; Gnel M. Mkrtchyan^a ; Ani S. Dadayan^a ; Satenik G. Petrosyan^b ; Arpine V. Geolchanyan^b ; Hayarpi M. Simonyan^b ; Anna F. Mkrtchyan^b ; Satenik Mkrtchyan^c ; Ashot Gevorgyan^c ; Viktor O. Iaroshenko^c ; ^d ; Peter Langer^c ; ^e ; ^{peter.langer@uni-rostock.de}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2013
• 出版时间：28 February, 2013
• 年：2013
• 卷：24
• 期：4
• 页码：229-232
• 全文大小：261 K

文摘

The conjugate addition of S-, N- and O-heterocyclic nucleophiles to the CC bond of dehydroalanine, bonded as a Schiff¡¯s base to the chiral auxiliary (S)-2-[N-(N¡ä-benzylprolyl)amino]benzophenone in the coordination sphere of Ni^II, resulted in the asymmetric synthesis of novel (S)-¦Á-aminopropionic acids containing a heterocyclic side chain, including imidazole, triazole, thiodiazole, thiazole and oxazole moieties (de 20-92 % ). After purification and cleavage of the metal complexes, the heterocyclic amino acids were isolated with high enantiomeric purity (ee >97 % ).