Diastereoselective spiroketalization: Stereocontrol using an iron(0) tricarbonyl diene complex

Organic Letters

Volumn 13, Issue 1, 2011, Pages 58-61

  Paley, Robert S ^a   Laupheimer, Madeleine C ^a   Erskine, Nathaniel A K ^a   Rablen, Paul R ^a   Pike, Robert D ^b   Jones, James S ^b  

^a SWARTHMORE COLLEGE   (United States)

^b The College of William and Mary   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650873040     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102472g     Document Type: Article

References (42)

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30. See Supporting Information for details.
31. Energies were computed at B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) and MP2/6-311+G(d,p)//B3LYP/6-31G(d). Energies reported in the text represent averages of these two different methods. Justification for this procedure is provided in the Supporting Information. Both proton NMR chemical shifts and proton-proton coupling constants were calculated using density functional theory. In general, the values calculated for the conformations shown agreed considerably more closely with experiment than did the values calculated for alternative conformations. See the Supporting Information for full details about the computational investigation.
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39. 1H NMR spectra for each of the major diastereomeric spiroketals 8a, 8b, and 14b - d display a more downfield chemical shift for the proton at C2 of the diene unit than in the corresponding minor diastereomer. Only in the case of spiroketal 14a does the major diastereomer display a more upfield shift for this proton, suggesting that the configuration at the spiroketal is opposite those of the other compounds. Furthermore, the major diastereomer of 14a is less polar by TLC than the minor diastereomer; in the other cases the major diastereomer is always more polar.
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