Cs2CO3-promoted efficient carbonate and carbamate synthesis on solid phase

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2797-2800

  Salvatore, Ralph N ^a   Flanders, Vincent L ^a   Ha, Dang ^a   Jung, Kyung Woon ^a  

^a H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; CESIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; AMINES; CARBAMATES; CARBONATES; CESIUM;

EID: 0034618290     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006212i     Document Type: Article

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35. Infrared spectra of all resin-bound carbonates were taken as KBr pellets and showed the indicative carbonyl stretching band in the appropriate locations for carbonates. The yield for the reactions were calculated on the basis of resin loading from gravimetric analysis after drying in vacuo over a 24 h time period. For a similar calculation, see the Supporting Information from the following reference: Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998.
36. -1.
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39. 2, and the optical rotations of the produced products were compared with starting materials as well as those reported. If any sterochemical sense was lost, it was to a negligible extent.
40. Carbonate products using Wang resin 13 were verified using infrared analysis (KBr pellet) showing the absence of the hydroxyl band. Also, the products were cleaved from the resin using triethylamine (10 equiv) in methanol, to yield the appropriate corresponding alcohols cleanly, which were compared to authentic samples by proton NMR analysis.
41. -1.
42. All carbamate products were verified by IR analysis, which indicated the appropriate carbonyl stretching band as well as the corresponding amide stretches.
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