Phosphine‐Promoted Cyclization of Dicyclopropenones

Yang, Jinming; Tang, Xiang‐Ying; Wei, Yin; Shi, Min

doi:10.1002/adsc.201300875

Cited by 14 publications

(6 citation statements)

References 52 publications

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“…In 2013, the Shi group disclosed a phosphine-catalyzed aldol-intervened RC reaction for the construction of various hexahydropentalen-2-ones. 152 The formation of the hexahydropentalen-2-ones can be controlled when employing dimethylphenylphosphine as the catalyst (Scheme 74). The reaction proceeds through initial nucleophilic addition of the phosphine to bis-cyclopropenone, generating the phosphonium enolate 27 .…”

Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

“…Although cyclopentenes are highly valued molecular motifs for secondary metabolite syntheses and pharmaceutical development, fused ring systems (e.g., hexahydropentalen-2-one) are equally important. In 2013, the Shi group disclosed a phosphine-catalyzed aldol-intervened RC reaction for the construction of various hexahydropentalen-2-ones . The formation of the hexahydropentalen-2-ones can be controlled when employing dimethylphenylphosphine as the catalyst (Scheme ).…”

Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

“…A different reaction pathway was followed when Shi and co-workers treated bis-cyclopropenones with 1,1-bis(diphenylphosphino)methane (dppm), forming several functionalized indanes (Scheme ). The reaction proceeded to give the zwitterion 421 , as discussed previously. After ring opening events, the intermediate 422 was formed.…”

Section: Ylides Formed Through Nucleophilic Addition Of Phosphinementioning

confidence: 99%

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Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

Section: Nucleophilic Phosphine Catalysis Of Alkenesmentioning

confidence: 99%

Section: Ylides Formed Through Nucleophilic Addition Of Phosphinementioning

confidence: 99%

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Phosphine Organocatalysis

et al. 2018

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“…Removal of the silyl group in 9a by n -Bu 4 NF afforded terminal alkyne 15 in 98% yield with >95:5 dr and 97:3 er (Scheme b). Sonogashira coupling of 15 was able to diversify the alkynyl moiety without erosion of stereoselectivity, solving the limitation on the scope of the alkynes . Click reaction of 15 provided 1,2,3-triazole 18 in 90% yield with 97:3 er .…”

Section: Resultsmentioning

confidence: 99%

Cobalt-Catalyzed Diastereo- and Enantioselective Carbon–Carbon Bond Forming Reactions of Cyclobutenes

Liang

Wang

et al. 2023

J. Am. Chem. Soc.

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Catalytic enantioselective functionalization of cyclobutenes constitutes a general and modular strategy for construction of enantioenriched complex cyclobutanes bearing multiple stereogenic centers, as chiral four-membered rings are common motifs in biologically active molecules and versatile intermediates in organic synthesis. However, enantioselective synthesis of cyclobutanes through such a strategy remained significantly limited. Herein, we report a series of unprecedented cobalt-catalyzed carbon–carbon bond forming reactions of cyclobutenes that are initiated through enantioselective carbometalation. The protocols feature diastereo- and enantioselective introduction of allyl, alkynyl, and functionalized alkyl groups. Mechanistic studies indicated an unusual 1,3-cobalt migration and subsequent β-carbon elimination cascade process occurred in the allyl addition. These new discoveries established a new elementary process for cobalt catalysis and an extension of diversity of nucleophiles for enantioselective transformations of cyclobutenes.

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“…In 2013, Shi's group presented a novel phosphine‐promoted intramolecular cyclization of dicyclopropenone 36 with the formation of phthalan 37 in 66 % yield. Reaction conditions include the use of THF as the solvent, H 2 O (1 equiv), and Me 2 PhP (1 equiv) as the ligand (Scheme ).…”

Section: Synthetic Routes To Phthalansmentioning

confidence: 99%

Recent Advances in Phthalan and Coumaran Chemistry

et al. 2018

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Oxygen‐containing heterocycles are common in biologically active compounds. In particular, phthalan and coumaran cores are found in pharmaceuticals, organic electronics, and other useful medical and technological applications. Recent research has expanded the methods available for their synthesis. This Minireview presents recent advances in the chemistry of phthalans and coumarans, with the goal of overcoming synthetic challenges and facilitating the applications of phthalans and coumarans.

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Phosphine‐Promoted Cyclization of Dicyclopropenones

Cited by 14 publications

References 52 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Cobalt-Catalyzed Diastereo- and Enantioselective Carbon–Carbon Bond Forming Reactions of Cyclobutenes

Recent Advances in Phthalan and Coumaran Chemistry

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