First dynamic kinetic resolution of selenium-containing chiral amines catalyzed by palladium (Pd/BaSO4) and Candida antartica lipase (CAL-B)

Tetrahedron Letters

Volumn 50, Issue 30, 2009, Pages 4331-4334

  Andrade, Leandro H ^a   Silva, Alexandre V ^a   Pedrozo, Eliane C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BARIUM SULFATE; PALLADIUM; SELENIUM DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CANDIDA ANTARCTICA; CATALYST; ENANTIOSELECTIVITY; ENZYME KINETICS; ONE POT SYNTHESIS; RACEMIZATION;

CANDIDA;

EID: 66449086922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.022     Document Type: Article

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25. 4. The solvent was removed in vacuum and the residue, containing the organoselenium amines, was acetylated with acetic anhydride for further HPLC analysis.
26. HPLC analysis for determination of the enantiomeric excess (ee): The enantiomeric purities of the organoselenium amides 5a-f were measured by HPLC analysis. The analysis was carried out on Chiralcel OD-H column and the peaks were detected by a UV detector at 254 nm. Eluent: hexane/isopropanol (95:5), flow rate: 1.0 mL/min. Retention times:(RS)-N-(1-(4-(Ethylselanyl)phenyl)ethyl)acetamide (5a): (R)-5a = 20.44 min; (S)-5a = 24.93 min.(RS)-N-(1-(4-(Methylselanyl)phenyl)ethyl)acetamide (5b): (R)-5b = 25.11 min; (S)-5b = 31.68 min.(RS)-N-(1-(4-(Butylselanyl)phenyl)ethyl)acetamide (5c): (R)-5c = 17.56 min; (S)-5c = 20.87 min.(RS)-N-(1-(4-(Benzylselanyl)phenyl)ethyl)acetamide (5d): (R)-5d = 56.46 min; (S)-5d = 63.76 min.(RS)-N-(1-(3-(Ethylselanyl)phenyl)ethyl)acetamide (5e): (R)-5e = 19.19 min; (S)-5e = 28.29 min.(RS)-N-(1-(2-(Ethylselanyl)phenyl)ethyl)acetamide (5f): (R)-5f = 16.92 min; (S)-5f = 44.46 min.
27. +: 372.0269, found 372.0266.