کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1348614 980361 2006 13 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
New chiral NiII complexes of Schiff’s bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
New chiral NiII complexes of Schiff’s bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids
چکیده انگلیسی

New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl)pyrrolidine-2-carboxamide (2-CBPB) and (S)-N-(2-benzoylphenyl)-1-(3,4-dimethylbenzyl)pyrrolidine-2-carboxamide (3,4-DMBPB) and their NiII complexes of Schiff’s base with glycine and alanine have been synthesized and tested in asymmetric C-alkylation and aldol condensation reactions of amino acid moieties. The tests proved that both new auxiliaries were efficient with the ee’s of the final amino acids as high as 98% even in case of α-methyl-α-amino acid synthesis.

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(S)-N-(2-Benzoylphenyl)-1-(2-chlorobenzyl)pyrrolidine-2-carboxamide hydrochlorideC25H23ClN2O2·HClEe pure[α]D20=-40.2 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-N-(2-Benzoylphenyl)-1-(3,4-dimethylbenzyl)pyrrolidine-2-carboxamide hydrochlorideC27H28O2N2·HClEe pure[α]D20=-38.5 (c 1.0, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-{({2-[1-(2-Chlorobenzyl)pyrrolidine-2-carboxamide]phenyl}phenylmethylene)-glicinato-N,N′,N″,O}nickel(II)C27H24ClN3NiO3Ee pure[α]D20=+2364 (c 0.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-{({2-[1-(3,4-Dimethylbenzyl)pyrrolidine-2-carboxamide]phenyl}phenylmethylene)-glycinato-N,N′,N″,O}nickel(II)C29H29N3NiO3Ee pure[α]D20=+1513 (c 0.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-{({2-[1-(2-Chlorobenzyl)pyrrolidine-2-carboxamide]phenyl}phenylmethylene)-(S)-alaninato-N,N′,N″,N}nickel(II)C28H26ClN3NiO3Ee pure[α]D20=+2574 (c 0.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(S)-{({2-[1-(3,4-Dimethylbenzyl)pyrrolidine-2-carboxamide]phenyl}phenylmethylene)-(S)-alaninato-N,N′,N″,O}nickel(II)C30H31N3NiO3Ee pure[α]D20=+2562 (c 0.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 3, 6 February 2006, Pages 455–467
نویسندگان
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