Origins of stereoselectivity in the Corey-Chaykovsky reaction. Insights from quantum chemistry

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4596-4606

  Lindvall, Mika K ^a   Koskinen, Ari M P ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHIRALITY; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; X RAY DIFFRACTION;

EID: 0033603506     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9818935     Document Type: Article

References (34)

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21. 2.
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24. The necessary stationary points of the model reaction were redetermined at this lower level of theory for the purpose of concistency.
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29. However, the solvation effect is 9 kcal/mol for 8 and 3 kcal/mol for 5, suggesting that 8 could be even more favored if optimization in solution had been available.
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31. A counterion would probably be present in typical applications of sulfonium methylides, lowering the energy of the starting materials. (29) They are stationary points at the HF/6-31G* level, as discussed in Results.
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33. Attempts to locate substituted version of B corresponding to trans-stilbene oxide formation at the HF/6-31G* level of theory were unsuccessful.
34. ar (ylide) torsional angle is defined by the carbon atoms in dark.