Photoinduced Vinylcyclopropane-Cyclopentene Rearrangement (Photo-VCP-CP): A Methodology for Chiral Bicyclo[3.2.0] heptenes and their Application in Natural Product Syntheses<sup>#</sup>

Sonawane, H. R.; Bellur, Nanjundiah S.; Kulkarni, D. G.; Ahuja, Jaimala R.

doi:10.1055/s-1993-22639

Cited by 49 publications

(13 citation statements)

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“…Variations of the method using Pd(0) catalysts had been developed [41][42][43] . They work in the presence of Pd(dba) 2 , dba = dibenzylideneacetone, and PPh 3 (0.05 equivalents) and proceed with high selectivity (30 -100% diastereomeric excess). Thus, (N-diphenylmethyleneamino)acetonitrile gives diastereoselectively pure trans-1-N-diphenylmethyleneamino-1-cyano-2-vinylcyclopropane in 74% yield within 15 min at room temperature (Scheme 4).…”

Section: Synthesis Of Vinylcyclopropanesmentioning

confidence: 99%

“…Vinylcyclopropanes (VCPs) are well known as important synthetic intermediates in organic transformations 1,2) and in the total synthesis of complex agents, for example, of steroids, pyrethroid insecticides or non-steroidal antiinflammatory agents [3][4][5] . Furthermore, many biologically active natural compounds show a vinylic cyclopropane substructure.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and polymerization of vinylcyclopropanes

Moszner

Zeuner

Völkel

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: Vinylcyclopropanes are important synthetic intermediates in organic chemistry and are mostly synthesized by the simultaneous introduction of the cyclopropane and the vinyl unit, e. g., by the reaction of trans-1,4-dihalobutenes with b -dicarbonyl compounds or the addition of carbenes to dienes. The polymerization of vinylcyclopropane itself results in vinyl polymers with predominantly 1,2-structural units. The radical polymerization of substituted vinylcyclopropanes results in polymers with mainly 1,5-ring-opened units, whereby radical stabilizing substituents or electron-withdrawing groups increase the radical polymerizability and the ring-opening ability. The vinylcyclopropanes undergo a radical copolymerization with other vinyl monomers, such as methacrylates, and, in comparison to the polymerization of these linear vinyl monomers, the vinylcyclopropanes show a significantly lower volume shrinkage during ring-opening polymerization. Hybrid vinylcyclopropanes are polymerized step-by-step under formation of reactive polymers or polymer networks. Multifunctional cross-linking vinylcyclopropanes can be used as new low-shrinking matrix monomers for photopolymerizable materials. In addition, the sol-gel process of trialkoxysilyl-functionalized vinylcyclopropanes affords low shrinking organic-inorganic nanocomposites.

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Section: Synthesis Of Vinylcyclopropanesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and polymerization of vinylcyclopropanes

Moszner

Zeuner

Völkel

et al. 1999

Macromol. Chem. Phys.

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“…The rearrangements of cyclopropyl ketones and aldehydes or vinyloxiranes have also found use in approaches to targets containing dihydrofurans. Reviews of the parent rearrangement and its heteroatom variants [7] as well as the somewhat related divinylcyclopropane-cycloheptadiene rearrangement [8] are available. It is curious to note the chronology of the discovery of this rearrangement and its heteroatom variants: the rearrangements of vinylcyclopropanes were last to be observed but first to be studied in detail following the initial reports.…”

Section: Originsmentioning

confidence: 99%

From Discovery to Application: 50 Years of the Vinylcyclopropane–Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products

2010

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A classic that hasn't lost its charm: The historical origins and current status of the vinylcyclopropane–cyclopentene rearrangement and the corresponding transformations of heteroatom‐containing analogues (see scheme) are described in the context of methodology development and natural products synthesis. Several important events that greatly influenced the author's own research program some 30 to 40 years ago are recounted as personal recollections.

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“…The reduction with lithium aluminum hydride was often used for confirmation of the structure and for establishment of the absolute configuration of naturally occurring substances [53,54]. For instance, a reduction of opically active epoxide epoxide 27 was studied in [23] (Scheme14).…”

Section: General Pattern Of Epoxy Compounds Reduction By Lithium Alummentioning

confidence: 99%

10.1007/s11178-008-2001-z

2010

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Analysis was performed of reduction processes of epoxy derivatives obtained from unsaturated compounds belonging to various groups: alkenes, cycloalkenes, spiroalkanes, and substituted norbornenes. The regio-and stereochemistry was discussed of reactions between epoxides and complex metal hydrides, of catalytic hydrogenation, and some other processes. The mechanisms were considered of the reduction reactions, in particular, those involving radical and ion radical intermediates.

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Photoinduced Vinylcyclopropane-Cyclopentene Rearrangement (Photo-VCP-CP): A Methodology for Chiral Bicyclo[3.2.0] heptenes and their Application in Natural Product Syntheses^#

Cited by 49 publications

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Synthesis and polymerization of vinylcyclopropanes

Synthesis and polymerization of vinylcyclopropanes

From Discovery to Application: 50 Years of the Vinylcyclopropane–Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products

10.1007/s11178-008-2001-z

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Photoinduced Vinylcyclopropane-Cyclopentene Rearrangement (Photo-VCP-CP): A Methodology for Chiral Bicyclo[3.2.0] heptenes and their Application in Natural Product Syntheses#

Cited by 49 publications

References 0 publications

Synthesis and polymerization of vinylcyclopropanes

Synthesis and polymerization of vinylcyclopropanes

From Discovery to Application: 50 Years of the Vinylcyclopropane–Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products

10.1007/s11178-008-2001-z

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Product

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Photoinduced Vinylcyclopropane-Cyclopentene Rearrangement (Photo-VCP-CP): A Methodology for Chiral Bicyclo[3.2.0] heptenes and their Application in Natural Product Syntheses^#