Improved procedures for the synthesis of (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB) and Ni(II) complexes of Schiff's bases derived from BPB and amino acids

被引:131
作者
Belokon', YN [1 ]
Tararov, VI [1 ]
Maleev, VI [1 ]
Savel'eva, TF [1 ]
Ryzhov, MG [1 ]
机构
[1] Russian Acad Sci, Inst Organoelement Cpds, Moscow 117813, Russia
关键词
D O I
10.1016/S0957-4166(98)00449-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(S)-N-Benzylproline (BP) was obtained by the reaction of (S)-proline and benzylchloride in high chemical yield (89%). (S)-2-[N-(N'-Benzylprolyl)amino]benzophenone (BPB) was synthesized in amounts greater than 100 g by the SOCl2 promoted condensation of BP with 2-aminobenzophenone (yield 82%). Ni(IT) complexes of Schiff's bases derived from BPB and amino acids were prepared by an improved procedure involving the use of KOH as a base and MeOH as solvent (yield 90-91%). (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4249 / 4252
页数:4
相关论文
共 7 条
  • [1] Belokon Y. N., 1992, JANSSEN CHIM ACTA, V2, P4
  • [2] CHIRAL COMPLEXES OF NI(II), CU(II), AND CU(I) AS REAGENTS, CATALYSTS AND RECEPTORS FOR ASYMMETRIC-SYNTHESIS AND CHIRAL RECOGNITION OF AMINO-ACIDS
    BELOKON, YN
    [J]. PURE AND APPLIED CHEMISTRY, 1992, 64 (12) : 1917 - 1924
  • [3] GENERAL-METHOD OF DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS BY CONDENSATION OF ALDEHYDES AND KETONES WITH GLYCINE
    BELOKON, YN
    BULYCHEV, AG
    VITT, SV
    STRUCHKOV, YT
    BATSANOV, AS
    TIMOFEEVA, TV
    TSYRYAPKIN, VA
    RYZHOV, MG
    LYSOVA, LA
    BAKHMUTOV, VI
    BELIKOV, VM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) : 4252 - 4259
  • [4] ASYMMETRIC-SYNTHESIS OF L-[BETA-C-11]AMINO ACIDS USING A CHIRAL NICKEL-COMPLEX OF THE SCHIFF-BASE OF (S)-O-[(N-BENZYLPROLYL)-AMINO]BENZOPHENONE AND GLYCINE
    FASTH, KJ
    LANGSTROM, B
    [J]. ACTA CHEMICA SCANDINAVICA, 1990, 44 (07): : 720 - 725
  • [5] STEREOSELECTIVITY IN THE TERNARY COMPLEXES COPPER(II)-N-BENZYL-L-PROLINE-D-ALPHA-AMINO-ACIDS OR L-ALPHA-AMINO-ACIDS
    JOZEFONVICZ, J
    MULLER, D
    PETIT, MA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1980, (01): : 76 - 79
  • [6] ASYMMETRIC ALDOL REACTIONS OF CHIRAL NI(II)-COMPLEX OF GLYCINE WITH ALIPHATIC-ALDEHYDES - STEREODIVERGENT SYNTHESIS OF SYN-(2S)-BETA-ALKYLSERINES AND SYN-(2R)-BETA-ALKYLSERINES
    SOLOSHONOK, VA
    AVILOV, DV
    KUKHAR, VP
    TARAROV, VI
    SAVELEVA, TF
    CHURKINA, TD
    IKONNIKOV, NS
    KOCHETKOV, KA
    ORLOVA, SA
    PYSAREVSKY, AP
    STRUCHKOV, YT
    RAEVSKY, NI
    BELOKON, YN
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1741 - 1756
  • [7] Synthesis of both enantiomers of beta,beta-diphenyl-alpha-alanine (Dip) from glycine using (S)- or (R)-2-[(N-benzylprolyl)amino]benzophenone as a reusable chiral auxiliary
    Tararov, VI
    Saveleva, TF
    Kuznetsov, NY
    Ikonnikov, NS
    Orlova, SA
    Belokon, YN
    North, M
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (01) : 79 - 83