- Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products
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A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.
- Wu, Yen-Ku,Lin, Rongrong,West
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- Efficient intermolecular 3+2 trapping of the Nazarov intermediate with vinyl sulfides
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Cross-conjugated 1,4-pentadien-3-ones undergo electrocyclization to 2-oxidocyclopentenyl cations upon treatment with BF3·OEt2. When these reactions are carried out in the presence of electron-rich vinyl sulfides, nucleophilic trappin
- Mahmoud, Bahja,West
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Read Online
- 2,2′-Biphenol/B(OH)3 catalyst system for Nazarov cyclization
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A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)3—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclo
- Sugimoto, Kenji,Oshiro, Miyu,Hada, Ryuhei,Matsuya, Yuji
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p. 1019 - 1022
(2019/09/12)
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- 1,4-Diketones from Cross-Conjugated Dienones: Potassium Permanganate-Interrupted Nazarov Reaction
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A domino potassium permanganate-interrupted Nazarov reaction to yield syn-2,3-disubstituted 1,4-diketones via a decarbonylative cleavage of the Nazarov oxyallyl intermediate, believed to be without precedent, is presented. This process allows syn substituents to be established stereospecifically on the 2-carbon bridge connecting the ketone carbonyl carbons, and the formation of one carbon-carbon and two carbon-oxygen bonds. Two carbon-carbon bonds are cleaved in this process.
- Kwon, Yonghoon,Schatz, Devon J.,West, Frederick G.
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supporting information
p. 9940 - 9943
(2015/08/19)
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- Synthesis of cyclopentenols and cyclopentenones via nickel-catalyzed reductive cycloaddition
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Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of
- Jenkins, Aireal D.,Herath, Ananda,Song, Minsoo,Montgomery, John
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supporting information; experimental part
p. 14460 - 14466
(2011/11/04)
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- Reagent-free Nazarov cyclisations
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A new protocol for Nazarov cyclisation is described that involves simple heating of dienones in the absence of any external Lewis acid. The Royal Society of Chemistry 2005.
- Douelle, Frederic,Tal, Lauren,Greaney, Michael F.
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p. 660 - 662
(2007/10/03)
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- Synthesis of Cyclopent-2-enones through Stepwise Cycloaddition of Simple Silyl Enol Ethers and Alk-1-ynes
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Treatment of silyl enol ethers and alk-1-ynes with SnCl4-Bu3N reagent followed by DBU, leads to cyclopent-2-enones, through cycloaddition reactions; the initial carbon-carbon bond formation is carbometallation of alkynes, and the second step is a base-promoted intramolecular alkylation which reductively eliminates tin species (DBU = 1,8-diazabicycloundec-7-ene).
- Yamaguchi, Masahiko,Sehata, Michiru,Hayashi, Akio,Hirama, Masahiro
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p. 1708 - 1709
(2007/10/02)
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