Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation

Pilho Kim, Michael H. Nantz, Mark J. Kurth, Marilyn M. Olmstead

Research output: Contribution to journalArticle

36 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1831-1834
Number of pages4
JournalOrganic Letters
Volume2
Issue number13
StatePublished - Jun 29 2000

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Alnus
Diels-Alder reactions
Cycloaddition Reaction
boats
Boats
Chemical activation
activation
Ships
room temperature
Substrates
Temperature

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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.

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 journalArticle

Kim, P, Nantz, MH, Kurth, MJ & Olmstead, MM 2000, 'Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation', Organic Letters, vol. 2, no. 13, pp. 1831-1834.
Kim, Pilho ; Nantz, Michael H. ; Kurth, Mark J. ; Olmstead, Marilyn M. / Intramolecular Diels-Alder reactions of decatrienoates : Remote stereocontrol and conformational activation. In: Organic Letters. 2000 ; Vol. 2, No. 13. pp. 1831-1834.
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