Stereocontrolled approach to 1,4-disubstituted 1,3-dienes

Trost, Barry M.; Godleski, Stephen A.; Ippen, Joachim

doi:10.1021/jo00418a001

Cited by 31 publications

(11 citation statements)

References 9 publications

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“…A stereocontrolled synthesis of a variety of oxygen- and sulfur-substituted dienes has also been realized by cycloreversion of substituted tricyclo[4.2.1.0 2,5 ]nonenes 314 (Scheme ) . Starting from endo- diester 312 , acyloin condensation readily gave endo- α-hydroxycyclobutanone 313 .…”

Section: Heterocyclic Five-membered Ring Compoundsmentioning

confidence: 99%

The Concept of Transient Chirality in the Stereoselective Synthesis of Functionalized Cycloalkenes Applying the Retro-Diels−Alder Methodology

1999

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Section: Heterocyclic Five-membered Ring Compoundsmentioning

confidence: 99%

The Concept of Transient Chirality in the Stereoselective Synthesis of Functionalized Cycloalkenes Applying the Retro-Diels−Alder Methodology

1999

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“…(c) Thermolyse des sulfones 5 Les thermolyses ont t t t effectutes en phase vapeur avec un temps de contact dans la zone chaude de I'ordre de 10 a 50 ms (pour une description de I'appareillage voir la reference 14). 11 a Ctt ntcessaire de chauffer a 650°C pour obtenir une conversion totale des sulfones 5.…”

Section: unclassified

“…Plusieurs mtthodes de synthese sttrtostlective des dienes-1,3 ont ett rtcemment decrites soit par reactions de Wittig modifites (3), soit par couplage croist d'un dtrivt organomttallique vinylique et d'un halogtnure vinylique de sttrtochimies bien definies (4), soit encore par ouverture thermique concertte de cyclobutknes substituts (5). Ces differentes mtthodes sont en gtntral difficilement applicables a la preparation de dienes fonctionnels.…”

Section: Introductionunclassified

Une synthèse hautement stéréosélective de diènes conjugués (E)

Bloch¹,

Abecassis²,

Hassan³

1984

Can. J. Chem.

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A general method for the preparation of (E) terminal conjugated dienes was developed by the flash thermolysis of 2-substituted 2,5-dihydrothiophene-1,1-dioxides generated by a retro Diels–Alder reaction. This process allows the obtention of conjugated dienes, bearing or not a functionality (alcohols, esters), with an excellent stereoisomeric purity (in general higher than 98%). An application to the synthesis of (E)-9,11-dodecadien-1-yl acetate, the major component of the sex pheromone of Diparopsiscastanea, shows the generality and the efficacy of this method.

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“…' The combination of different electron-attracting groups on the dienophile (E or Z), as indicated above, opens a way to the stereo-specific construction of synthetically useful cyclohexenes. The preparation of several types of dienes has been reported (13).…”

Section: C02ch3 02n (C02ch3mentioning

confidence: 99%