Triphenylphosphine promoted addition of acetylenic esters to benzofuran-2,3-dione: One-pot synthesis of novel γ-spirolactones

Esmaili, Abbas Ali; Nasseri, Mohammad Ali; Vesalipoor, Hamid

doi:10.3998/ark.5550190.0009.f30

Cited by 14 publications

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Winterfeldt reaction can also be performed using benzofuran-2,3-diones and phthalic anhydrides as electrophile partners (Scheme 460). 533,534 Esmaili and Bayat demonstrated the synthesis of spirobenzofuran-2-ones and spirophthalans with good efficiencies and tolerance for various substituents on the benzene ring system. catalysis between alkynoates and ketones (Scheme 461).…”

Section: S N 2′/s N 2-michael Annulationmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

View full text Add to dashboard Cite

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.

show abstract

Section: S N 2′/s N 2-michael Annulationmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

View full text Add to dashboard Cite

show abstract

Catalytic Asymmetric Synthesis of Chiral Benzofuranones

Cheng

2014

Adv Synth Catal

View full text Add to dashboard Cite

The chiral benzofuranone structural motif is a prominent feature in many natural products, which exhibit a broad range of biological and pharmaceutical activities. In the past few years, a survey of chiral benzofuranone derivatives based on asymmetric catalysis reveals an increasing number of papers, which reflects the latest achievements to facilitate the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. Recent advances in this area are summarized and classified according to the structure of the starting substrate.

show abstract