Abstract
(Formula presented) The intramolecular Diels-Alder (IMDA) reactions of C(8)-substituted decatrienoates have been studied. The stereospecific formation of 11 via an endo-boat-9 transition state attests to the powerful directing influence of a C(8) substituent in the IMDA of decatrienoate. In addition, the contrasting observations that stereospecific 9 → 11 occurs at room temperature while the nor-tert-butyl substrate (4a) requires 125 °C/5 h reaction conditions and produces a 60:40 mixture of diastereomers provide clear evidence that a bulky C(8) substituent is a powerful conformational activator of the IMDA.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1831-1834 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 2 |
| Issue number | 13 |
| State | Published - Jun 29 2000 |
ASJC Scopus subject areas
- Molecular Medicine
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Kim, P., Nantz, M. H., Kurth, M. J., & Olmstead, M. M. (2000). Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation. Organic Letters, 2(13), 1831-1834.