Syn-anti isomerization of aldols by enolization

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3671-3673

  Ward, Dale E ^a   Sales, Marcelo ^a   Sasmal, Pradip K ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

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EID: 0000727245     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016581u     Document Type: Article

References (39)

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34. Chloroform solutions were not stable to prolonged heating.
35. 4 (retroaldol mechanism).
36. Ward, D. E.; Guo, C.; Sasmal, P. K.; Man, C. C.; Sales, M. Org. Lett. 2000, 2, 1325-1328.
37. There are 20 diastereomers possible for 11. In principle, all diastereomers could be produced from 11aa or 11sa via a retroaldol-aldol mechanism, whereas enolization can only interconvert the three diastereomers shown.
38. In some experiments, a small amount (1-3%) of aldehyde 4 was detected after prolonged reaction.
39. obs) vs ln([imidazole]) for entries 4, 6, 7, and 10. Regression analysis on these four data points yields a slope of 1.28 ± 0.13 (95% confidence interval).