Bioactive Heterocycles from Domino Wittig-Pericyclic Reactions

Schobert, Rainer; Gordon, G. J.

doi:10.2174/1385272023373563

Cited by 30 publications

(7 citation statements)

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“…A more complete study on the scope of this cascade sequence has been reported, 87 and the application of domino Wittig-pericyclic reactions to bioactive heterocycles has recently been reviewed. 88 The stereoselective formation of imidazolidine thiones via the rearrangement of chiral thiocyanates have recently been reported. Heating allylic thiocyanates such as 254 at 80 °C for 3 h produced 1:1-mixtures of diastereomeric isothiocyanates 255 in 92% yield (Scheme 52).…”

Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

The domino way to heterocycles

Padwa¹,

Bur²

2007

Tetrahedron

391

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Sequential transformations enable the facile synthesis of complex target molecules from simple building blocks in a single preparative step. Their value is amplified if they also create multiple stereogenic centers. In the ongoing search for new domino processes, emphasis is usually placed on sequential reactions which occur cleanly and without forming by-products. As a prerequisite for an ideally proceeding one-pot sequential transformation, the reactivity pattern of all participating components has to be such that each building block gets involved in a reaction only when it is supposed to do so. The development of sequences that combine transformations of fundamentally different mechanisms broadens the scope of such procedures in synthetic chemistry. This mini review contains a representative sampling from the last 15 years on the kinds of reactions that have been sequenced into cascades to produce heterocyclic molecules.

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Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

The domino way to heterocycles

Padwa¹,

Bur²

2007

Tetrahedron

391

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“…The prospects of multi-step, one-pot reactions and reaction cascades incorporating Wittig reagents can be seen in the rich chemistry of ketenylidenetriphenylphosphorane (178) (Scheme 45) [182][183][184][185], which has been reviewed earlier [182,186,187]. Lastly, catalytic Wittig reactions can be seen as a subset of tandem reactions involving phosphoranes.…”

Section: Resultsmentioning

confidence: 99%

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Merza¹,

Taha²,

Thiemann³

2018

Alkenes

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The Wittig olefination utilizing phosphoranes and the related Horner-WadsworthEmmons (HWE) reaction using phosphonates transform aldehydes and ketones into substituted alkenes. Because of the versatility of the reactions and the compatibility of many functional groups towards the transformations, both Wittig olefination and HWE reactions are a mainstay in the arsenal of organic synthesis. Here, an overview is given on Wittig-and Horner-Wadsworth-Emmons (HWE) reactions run in combination with other transformations in one-pot procedures. The focus lies on one-pot oxidation Wittig/HWE protocols, Wittig/HWE olefinations run in concert with metal catalyzed cross-coupling reactions, Domino Wittig/HWE-cycloaddition and Wittig-Michael transformations.

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“…We have demonstrated that the established synthesis of E-a; b-unsaturated esters from alcohols, aldehydes and the cumulated ylide Ph 3 PCCO [30] is also applicable to hydroxy functionalized alkene-carbene complexes of chromium. This should be a rather general method for the attachment of multiply functionalized side-chains to preformed carbene complexes via an ester linkage.…”

Section: Discussionmentioning

confidence: 99%