Asymmetric nitroaldol reaction using nitromethane labeled with 11C

Tetrahedron Letters

Volumn 49, Issue 41, 2008, Pages 5837-5839

  Kato, Koichi ^a,b   Gustavsson, Sven Åke ^a,c   Långström, Bengt ^a,c  

^a UPPSALA UNIVERSITY   (Sweden)

^b NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^c BIACORE AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 11; LANTHANUM; LITHIUM; NITROMETHANE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL LABELING; CHIRALITY; ISOTOPE LABELING; RADIOASSAY;

EID: 50049104416     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.074     Document Type: Article

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22. 3I (around or higher than 37 GBq/μmol) due to no isotope contamination during nitration reaction.
23. 3I through a column filled with silver nitrite at 70 °C and dried potassium carbonate. 1 was trapped in a 0.03 M catalyst solution in THF (300 μL). The reaction mixture was placed in a cooling bath and 5 μL of the aldehyde was added. After 5 min, a saturated solution of aqueous ammonium chloride (100 μL) was added to quench the reaction mixture. The contents of the vial were diluted and the formed product was purified by semi-preparative HPLC.
24. 3 (2.5 mL, 0.5 mmol) in THF was added at room temperature. After mixture was stirred overnight, water (9 μL, 0.5 mmol) was added and the resulting catalyst solution was stored at room temperature.
25. 1H NMR was measured for a mixture of 4 and non-labeled 6. Non-labeled 6 was detected by GC and HPLC in the mixture. Yield was determined by HPLC using methyl 4-chlorocinnamate as an internal standard. Ee was determined by HPLC using CHIRALPAK AD-H (DAICEL).
26. Shibasaki et al. reported that using other lanthanide metal for catalysts gave corresponding nitroaldol product in good ee for this reaction. Details are described in Ref. 8d.
27. Li C.-J. Chem. Rev. 105 (2005) 3095-3165