Polymer-supported organocatalysts: Asymmetric reduction of imines with trichlorosilane catalyzed by an amino acid-derived formamide anchored to a polymer

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 3985-3995

  Malkov, Andrei V ^a   Figlus, Marek ^a   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINATION; AMINES; AMINO ACIDS; CATALYSIS; CATALYST ACTIVITY; CHEMICAL REACTIONS; CHEMICALS; COMPUTER NETWORKS; ENANTIOSELECTIVITY; HEALTH; LAND USE; MICROFLUIDICS; NETWORK PROTOCOLS; NITROGEN COMPOUNDS; ORGANIC ACIDS; ORGANIC COMPOUNDS;

AMERICAN CHEMICAL SOCIETY (ACS); ASYMMETRIC REDUCTION; CATALYST LOADINGS; CHEMICAL EQUATIONS; CHIRAL AMINES; FORM AMIDES; KETIMINES; MULTIPLE USE; ORGANOCATALYSTS; PARALLEL SYNTHESIS; POLYMER-SUPPORTED; POLYMER-SUPPORTED CATALYSTS; ROOM-TEMPERATURE (RT); TRICHLOROSILANE;

POLYMERS;

AMINO ACID; IMINE; POLYMER; SILANE DERIVATIVE; TRICHLOROSILANE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; ORGANIC CHEMISTRY; REDUCTION; SYNTHESIS;

AMINO ACIDS; CATALYSIS; FORMAMIDES; IMINES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; POLYMERS; SILANES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED;

EID: 44949212976     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800094q     Document Type: Article

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68. The following resins were employed in this study: (a) Chloromethyl-polystyrene (24) 1.23 mmol/g 75-150 μm (StratoSphere), obtained from Polymer Laboratories. (b) 5-[4-(Chloromethyl)phenyl]pentyl]styrene (25), polymer-bound 0.75-1.25 mmol/g 100-200 μm, obtained from Aldrich. (c) Bromomethylphenoxymethyl polystyrene (26) 1.40 mmol/g (StratoSphere) 150-300 μm, obtained from Polymer Laboratories. (d) 4-Hydroxymethylphenoxymethyl polystyrene (27) 1.70 mmol/g (StratoSphere) 150-300 μm, obtained from Polymer Laboratories. (e) TentaGel HL Br resin (28), 0.43 mmol/g, 110 μm, obtained from Rapp Polymere GmbH. (f) TentaGel HL OH resin (29) 0.43 mmol/g 110 μm, obtained from Rapp Polymere GmbH. (g) 4-Hydroxytiophenol resin (30), 1.58 mmol/g, 150-300 μm (StratoSphere), obtained from Polymer Laboratories.
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70. The reaction carried out at 45°C gave 5a in 62% yield, whereas at 80°C the yield decreased to 31%. The use of THF or various mixtures of THF and DMF as solvent, gave inferior results.
71. Dichloromethane behaved in a similar way as chloroform, exhibiting only slightly lower enantioselectivities. On the other hand, solvents such as THF or MeCN proved to be unsuitable for homogeneous solutions and were, therefore, excluded from this study.