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Al_2O_3催化下的取代β-羟基胺Schiff碱衍生物的C—C键裂解反应

The Al_2O_3 Catalyzed C—C Bond Cleavage of β-amino Alcohol Schiff Base Derivatives
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摘要 探讨了中性Al2O3催化下的取代β-羟基胺Schiff碱衍生物的C—C键裂解反应,结果表明,在Al2O3存在下,由取代苯甲醛与1,2-二苯基-2-氨基乙醇形成的亚胺类化合物很容易通过逆ene反应过程发生α,β-C—C键断裂,且反应不受芳醛分子中邻位基团的影响.通过跟踪反应进程,提出了可能的反应机理. The Al2O3 catalyzed C C bond cleavage of β-amino alcohol Schiff base derivatives is discussd. It is found that the α,β-C C bond of the Schiff base formed by substituted benzaldehydes and β-amino alcohol derivatives can cleave easily via a retro-ene process in the presence of Al2O3 and the cleavage is not affected by the neighboring group. A proposal mechanism is therefore suggested.
机构地区 郑州大学化学系
出处 《郑州大学学报(理学版)》 CAS 2006年第3期74-78,共5页 Journal of Zhengzhou University:Natural Science Edition
基金 国家自然科学基金资助项目 编号20372059
关键词 AL2O3 催化 Β-氨基醇 SCHIFF碱 C—C键裂解 Al2O3 ,catalysis β-amino alcohol Schiff base C- C bond cleavage
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参考文献11

  • 1JACKSON E L.Periodic acid oxidation[J].Organic Reactions,1944,2:341-375.
  • 2MOSETTIG E.The synthesis of aldehydes from carboxylic acids[J].Organic Reactions (New York),1954,3:218-257.
  • 3OHLOFF G,GIERSCH W.Conversion of vicinal diols into dicarbonyl compounds by manganese dioxide[J].Angewandte Chemie,1973,12(5):401-402.
  • 4CISNEROS A,FERNANDEZ S,HERNANDEZ J E.Cleavage of vicinal diols by pyridinium chlorochromate[J].Synthetic Communications,1982,12 (11):833-838.
  • 5HOUSE H O,BERKOWITZ W F.The stereochemistry of the Neber rearrangement[J].J Org Chem,1963,28(9):2271-2276.
  • 6KOVAR J,JARY J,BLAHA K.The configuration of nitrogen-containing compounds(XVI):the oxidation of amino alcohols with periodic acid[J].Coll Czech Chem Commun,1963,28(8):2199-2206.
  • 7SHIMIZU M,MAQINO H.Oxidative carbon-carbon bond cleavage reaction of 1,2-diamines and 1,2-amino alcohols under an oxygen atmosphere[J].Tetrahedron Letters,2001,42 (50):8865-8868.
  • 8BLAY G,FERNANDEZ I,MARCO-ALEIXANDRE A,et al.Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis,Ti(Ⅳ)catalyzed enantioselective addition of diethylzinc to aldehydes[J].Tetrahedron:Asymmetry,2005,16(6):1207-1213.
  • 9GISSIBL A,FINN M G,REISER O.Cu(])-aza(bisoxazoline)-catalyzed asymmetric benzoylations[J].Organic Letters,2005,7(12):2325-2328.
  • 10陶京朝,弓建红,刘玉霞,樊亚芳,刘宏民.1,2-二苯基-2-氨基乙醇的合成与机理研究[J].郑州大学学报(理学版),2004,36(2):76-79. 被引量:4

二级参考文献10

  • 1Zhou Haibing, Zhang Ji, Lu Shoumao ,et al. Design ,synthesis and structure of new chiral squaric acid momo-aminoalcohols and diaminoalcohols and their use as catalysts in asymmetric reduction of ketones and diketones. Tetrahedron,2001, 57(45): 9325~9333.
  • 2Andrés Jose M, Pedrosa Rafael, Pérez-Encabo Alfonso. Synthesis of chiral, non-race micaldols from chiral β-hydroxyweinreb amides prepared by enantioselective reformatsky-like reaction induced by chiral β-aminoalcohols. Tetrahedron,2000, 56(9): 1217~1
  • 3Henry Gilman. Benzoin Organic Synthesis (Collected Volume). New York: John Wiley INC, 1941.94.
  • 4Nishimra S, Urushibara Y. A method for the preparation of the Raney nichel catalyst with a greater activity. Bull Chem Soc Jpn, 1957, 30(2): 199.
  • 5Oscar Pamies, Jan E Backvall. Combination of enzymes and metal catalyst:a powerful approach in asymmetric catalysis. Chem Rev , 2003, 103(8): 3247-3257.
  • 6Desimoni Giovanni, Faita Giuseppe, Guala Matilde, et al. The stereo-divergent synthesis of chiral 4,5-disubstituted pybox ligand. Tetrahedron:Asymmetry,2002 ,13 (15): 1651-1654.
  • 7Patti Angela, Pedotti Sonia . Screening of chiral ferrocenyl amino alcohols as ligands for ruthenium-catalysed transfer hydrogenation of ketones. Tetrahedron :Asymmetry, 2003 , 14 (5): 597- 602.
  • 8Kaoru Harada. Stereoselective catalytic hydrogenation of α-hydroxyketoxines. Bull Chem Soc Jpn, 1984, 57(4): 1040-1045.
  • 9Wolf Christian, Francis Christopher J, Hawes Pili A, et al. Enantioselective alkylation of aldehydes promoted by (S)tyrosine-derived β-amino alcohols. Tetrahedron: Asymmetry, 2002, 13(16): 1733- 1741.
  • 10Jion Weijilard, Karl Pfister, Swanezy E F, et al. Preparation stereoisomeric α,β-diphenyl-β-hydroxyethylamines. J Am Chem Soc, 1951, 73 (2): 1218-1216.

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