Synthesis and characterization of new chiral ketopinic acid-derived catalysts immobilized on polystyrene-bound imidazole

Open access

Abstract

Four new chiral ketopinic acid-derived catalysts were anchored on a polystyrene-bound imidazole via non-covalent bond. The resulting heterogeneous catalysts were successfully characterized using IR, SEM, and TGA analyses.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • [1]. Y. Hassan Synthesis of chiral ketopinic acidderived catalysts and their evaluation in asymmetric transformations PhD Thesis Rhodes University pp. 1-173 (2015).

  • [2]. P.G. Hultin L.M. Geary The state of the art in asymmetric induction: the aldol reaction as a case study Tetrahedron: Asymmetr. 20 (2009) 131-173. DOI: 10.1016/j.tetasy.2008.12.030

  • [3]. A. Córdova W. Zou I. Ibrahem E. Reyes M. Engqvist W.W. Liao Acyclic amino acidcatalyzed direct asymmetric aldol reactions: alanine the simplest stereoselective organocatalyst Chem. Commun. 28 (2005) 3586-3588. DOI: 10.1039/B507968N

  • [4]. C. Li X.W. Feng N. Wang Y.J. Zhou X.Q. Yu Biocatalytic promiscuity: the first lipasecatalysed asymmetric aldol reaction Green Chem. 10 (2008) 616-618. DOI: 10.1039/B803406K

  • [5]. Y.L. Liu B.L. Wang J.J. Cao L. Chen Y.X. Zhang C. Wang J. Zhou Organocatalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles via Morita−Baylis−Hillman reaction J. Am. Chem. Soc. 132 (2010) 15176-15178. DOI: 10.1021/ja107858z

  • [6]. D.V. Basavaiah B.S. Reddy S.S. Badsara Recent contributions from the Baylis−Hillman reaction to organic chemistry Chem. Rev. 110 (2010) 5447-5674. DOI: 10.1021/cr900291g

  • [7]. Q. Gu S.L. You Desymmetrization of cyclohexadienones viacinchonine derived thiourea-catalyzed enantioselective aza- Michael reaction and total synthesis of (-)- mesembrine Chem. Sci. 2 (2011) 1519-1522. DOI: 10.1039/C1SC00083G

  • [8]. Z. Amara J. Caron D. Joseph Recent contributions from the asymmetric aza- Michael reaction to alkaloids total synthesis Nat. Prod. Rep. 30 (2013) 1211-1225. DOI: 10.1039/C3NP20121J

  • [9]. A. Jakoblinnert R. Mladenov A. Paul F. Sibilla U. Schwaneberg M.B. Ansorge- Schumacher P.D. de María Asymmetric reduction of ketones with recombinant E. coli whole cells in neat substrates Chem. Commun. 47 (2011) 12230-12232. DOI: 10.1039/C1CC14097C

  • [10]. Z.H. Yang L. Luo X. Chang W. Zhou G.H. Chen Y. Zhao Y.J. Wang Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction J. Ind. Microbiol. Biotechnol. 39 (2012) 835-841. DOI: 10.1007/s10295-012-1088-y

  • [11]. M. Hayashi T. Tamura M. Shoji The chiral diamine mediated asymmetric Baylis-Hillman reaction Adv. Synth. Catal. 346 (2004) 1106-1110. DOI: 10.1002/adsc.200404069

  • [12]. (a) G. Cardillo C. Tomasini Asymmetric synthesis of ß-amino acids and α-substituted β- amino acids Chem. Soc. Rev. 25 (1996) 117-128. DOI: 10.1039/CS9962500117 (b) F.F. Blicke Mannich reaction Org. React. 1 (1942) 303. DOI:10.1002/0471264180.or001.10 (c) M. Tramontini L. Angiolini Further advances in the chemistry of Mannich bases Tetrahedron 46 (1990) 1791-1837. DOI: 10.1016/S0040-4020(01)89752-0 (d) M. Arend B. Westermann N. Risch Modern variants of the Mannich reaction Angew. Chem. Int. Ed. 37 (1998) 1044-1070. DOI: 10.1002/(SICI)1521-3773(19980504)37 (e) S. Kobayashi H. Ishitani Catalytic enantioselective addition to imines Chem. Rev. 99 (1999) 1069-1094. DOI: 10.1021/cr980414z

  • [13]. T.S. Reger K.D. Janda Polymer-supported (salen)Mn catalysts for asymmetric epoxidation: A comparison between soluble and insoluble matrices J. Am. Chem Soc. 122 (2000) 6929-6934. DOI: 10.1021/ja000692r

  • [14]. H. Han K.D. Janda Soluble polymer-bound ligand-accelerated catalysis: asymmetric dihydroxylation J. Am. Chem Soc. 118 (1996) 7632-7633. DOI: 10.1021/ja9608095

  • [15]. B.B. De B.B. Lohray S. Sivaram P.K. Dhal Polymeric catalysts for chemo- and enantioselective epoxidation of olefins: New crosslinked chiral transition metal complexing polymers J. Polym. Sci. A-Polym. Chem. 35 (1997) 1809-1818. DOI: 10.1002/(SICI)1099-0518(19970715)35

  • [16]. K.S. Yang W.D. Lee J.F. Pan K. Chen Chiral Lewis acid - catalyzed asymmetric Baylis − Hillman reactions J. Org. Chem. 68 (2003) 915-919. DOI: 10.1021/jo026318m

  • [17]. R.I. Kureshy N. Khan S. Abdi P. Iyer A. Bhatt Enantioselective catalytic epoxidation of nonfunctionalized prochiral olefins by dissymmetric chiral Schiff base complexes of Mn(III) and Ru(III) metal ions II J. Mol. Cat. A-Chem. 120 (1997) 101-108. DOI: 10.1016/S1381-1169(96)00432-3

  • [18]. R.B. Merrifield Solid phase peptide synthesis. I. The synthesis of a tetrapeptide J. Am. Chem. Soc. 85 (1963) 2149-2154. DOI: 10.1021/ja00897a025

  • [19]. V. Mirkhani M. Moghadam S. Tangestaninejad B. Bahramian Polystyrenebound imidazole as a heterogeneous axial ligand for Mn(salophen)Cl and its use as biomimetic alkene epoxidation and alkane hydroxylation catalyst with sodium periodate Appl. Catal. AGen. 311 (2006) 43-50. DOI: 10.1016/j.apcata.2006.05.043

  • [20]. M.L. Linares N. Sanchez R. Alajaran J.J. Vaquero J.A. Builla Solid-support-bound 1- aminoimidazolium chlorochromate: A selective efficient and recyclable oxidant Synthesis 3 (2001) 382-388. DOI: 10.1055/s-2001-11431

Search
Journal information
Metrics
All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 257 145 2
PDF Downloads 113 88 1