A straightforward synthesis of conhydrine by hetero Diels–Alder strategy mediated by microwaves

Bandini, Elisa; Corda, G; D'Aurizio, Antonio; Panunzio, Mauro

doi:10.1016/j.tetlet.2009.12.039

Cited by 15 publications

(9 citation statements)

References 31 publications

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“…In similar way, by applying hetero-Diels-Alder cycloaddition under MW conditions, Bandini et al obtained novel conhydrines [100]. The [4 + 2]-cycloaddition of an azadiene (264), prepared in two conventional steps from the corresponding aldehyde, with sulfone moiety 265 under MW conditions furnished the expected cycloadducts 266 and 267 in 82% chemical yields and 50:50 diastereomeric ratio (Scheme 17.45).…”

Section: Intermolecular Hetero-diels-alder Reactionsmentioning

confidence: 93%

Microwave‐Assisted Cycloaddition Reactions

Bougrin

Benhida

2012

Microwaves in Organic Synthesis

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Section: Intermolecular Hetero-diels-alder Reactionsmentioning

confidence: 93%

Microwave‐Assisted Cycloaddition Reactions

Bougrin

Benhida

2012

Microwaves in Organic Synthesis

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“…reacts with 1,1-BPSE (6)t og enerate cycloadduct 184.A fter separation of the diastereomers, removal of the sulfones using sodium amalgam followed by reduction of the lactam afforded both (À)-a-(185)a nd (À)-b-conhydrine (186). [65] Acetylene equivalent…”

Section: Ethylenee Quivalentmentioning

confidence: 99%

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small‐Molecule Synthons

Trost

Kalnmals

2019

Chemistry A European J

129

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Sulfones are flexible functional groups that can act as nucleophiles, electrophiles, or even radicals. Changing the reaction conditions can completelya lter the reactivity of as ulfonyl group, and as ar esult, molecules bearing multiple sulfones are versatile building blocks. This Review highlights the unique ability of 1,1-and 1,2-bis(sulfones) to masquerade as av ast array of reactive synthons includingm ethane polyanions, vinyl cations,a nd all-carbond ipoles that would be difficultori mpossible to access directly.Scheme1.Selectedsyntheses and reactions of sulfones.Scheme2.Seminaluse of abis(sulfone) as am ethanedianion equivalent.[a] Prof. 11195 MinireviewScheme5.Pd-catalyzed allylic alkylation reactionsw ith bis(sulfones) as methylanion equivalents.Scheme6.Mitsunobumethylationfacilitated by ab is(sulfone) nucleophile.Scheme7.Formal methyl conjugate additiont oa,b-unsaturated aldehydes.Scheme8.Formal methyl conjugate additiont oa na,b-unsaturated ketone.Scheme11. Organocatalytic asymmetric allylic alkylation of Morita-Baylis-Hillmanc arbonates with FBSM.Scheme12. Formal asymmetric fluoromethylationofa ldimines.Scheme13. Formal asymmetric fluoromethylationofa ldehydes.Scheme14. Formal fluoromethylconjugate additionst oenals.Scheme15. Formal fluoromethylconjugate addition to enones.Scheme16. Alkylation of FBSM with alcohols and alkyl halides.Scheme17. Differential reactivity of BDT in difficult alkylation reactions.Scheme18. Annulative Mitsunobu reactionswith bis(sulfone) nucleophiles.Scheme19. Macrocyclizationr eactionsf acilitated by bis(sulfones). Scheme20. Syntheses of insect pheromones facilitated by bis(sulfones).Scheme21. To talsynthesis of (À)-trans-lauthisan.Scheme22. To talsyntheses of constanolactones Aand B.Scheme56. Usingabis(sulfone) to access an ambiphilic carbonyl synthon.Scheme57. Usingabis(sulfone) to access ac arbonyl diradical synthon.Scheme58. Syntheses of (AE)-21-noribogamineand (AE)-ibogamine facilitated by using abis(sulfone) as areplacement for lowmolecular weight olefins.

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“…Bandini et al (2010) developed a method for the synthesis of optically active conhydrines by hetero-Diels-Alder cycloaddition reaction mediated by microwaves.…”

Section: Diels-alder Additionmentioning

confidence: 99%

Elimination

2014

Microwave-Assisted Organic Synthesis

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A straightforward synthesis of conhydrine by hetero Diels–Alder strategy mediated by microwaves

Cited by 15 publications

References 31 publications

Microwave‐Assisted Cycloaddition Reactions

Microwave‐Assisted Cycloaddition Reactions

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small‐Molecule Synthons

Elimination

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