A New Convenient Synthesis of Ethenyl Ethers

Cabianca, Elena; Chéry, Florence; Rollin, Patrick; Cossu, Sergio; Lucchi, Ottorino De

doi:10.1055/s-2001-18757

Cited by 18 publications

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“…In the first step of the sequence, alcohols add across the alkene in 7E through an addition-elimination mechanism and in the second step, the remaining sulfone is cleaved. [77] In ar elated process, Dietrich showedt hat salicylaldehydes 254 react with bis(sulfone) 1 to generate benzofurans 257 (Scheme 50 b). After condensation of 1 with 254,t he phenolate ion in 255 undergoes anti-Michael addition to the pendant alkylidene bis(sulfone).…”

Section: Scheme46 Synthesis Of Dihydrojasmoneusing Ab Is(sulfone) Asmentioning

confidence: 99%

“…For example, De Lucchi disclosed a two‐step synthesis of vinyl ethers ( 251 – 253 ) that uses 1,2‐BPSE 7E as an ethylene cation synthon (Scheme a). In the first step of the sequence, alcohols add across the alkene in 7E through an addition–elimination mechanism and in the second step, the remaining sulfone is cleaved . In a related process, Dietrich showed that salicylaldehydes 254 react with bis(sulfone) 1 to generate benzofurans 257 (Scheme b).…”

Section: Synthetic Equivalents Of Sp2 and Sp Synthonsmentioning

confidence: 99%

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

Trost

Kalnmals

2019

Chemistry A European J

108

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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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Section: Scheme46 Synthesis Of Dihydrojasmoneusing Ab Is(sulfone) Asmentioning

confidence: 99%

Section: Synthetic Equivalents Of Sp2 and Sp Synthonsmentioning

confidence: 99%