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 |
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ASJC Scopus subject areas
- Molecular Medicine
Cite this
Intramolecular Diels-Alder reactions of decatrienoates : Remote stereocontrol and conformational activation. / Kim, Pilho; Nantz, Michael H.; Kurth, Mark J.; Olmstead, Marilyn M.
In: Organic Letters, Vol. 2, No. 13, 29.06.2000, p. 1831-1834.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Intramolecular Diels-Alder reactions of decatrienoates
T2 - Remote stereocontrol and conformational activation
AU - Kim, Pilho
AU - Nantz, Michael H.
AU - Kurth, Mark J.
AU - Olmstead, Marilyn M.
PY - 2000/6/29
Y1 - 2000/6/29
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=0000809370&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0000809370&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0000809370
VL - 2
SP - 1831
EP - 1834
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 13
ER -