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

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

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

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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title = "Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation",

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.",

author = "Pilho Kim and Nantz, {Michael H.} and Kurth, {Mark J.} and Olmstead, {Marilyn M.}",

year = "2000",

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language = "English (US)",

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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.

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M3 - Article

AN - SCOPUS:0000809370

VL - 2

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EP - 1834

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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ER -

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

Abstract

ASJC Scopus subject areas

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