Journal ArticleDOI
Phosphine-Catalyzed Enantioselective [4 + 3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles
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TLDR
The first catalytic enantioselective [4 + 3] annulation of allenoates with C,N-cyclic azomethine imines is developed, which works efficiently under mild reaction conditions to afford seven-membered ring-fused quinazoline-based tricyclic heterocycles in high yields with good to excellent diastereo- and enantiOSElectivities.About:
This article is published in Organic Letters.The article was published on 2016-10-21. It has received 71 citations till now. The article focuses on the topics: Annulation & Quinazoline.read more
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Phosphine-Catalyzed Asymmetric Organic Reactions.
TL;DR: This review summarizes all of the literature examples from late 1990s to the end of 2017, alongside their mechanistic insights whenever possible, with a very aim to trigger more intensive research in the future to render asymmetric phosphine catalysis one of the most common and reliable tools to organic chemists.
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Enantioselective Phosphine-Catalyzed Formal [4+4] Annulation of α,β-Unsaturated Imines and Allene Ketones: Construction of Eight-Membered Rings
TL;DR: This work marks the first efficient asymmetric construction of optically enriched eight-membered rings by phosphine catalysis, in excellent yields and with nearly perfect enantioselectivities.
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Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates
TL;DR: The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities.
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Asymmetric (4 + 3) and (4 + 1) Annulations of Isatin-derived Morita–Baylis–Hillman Carbonates to Construct Diverse Chiral Heterocyclic Frameworks
TL;DR: A chiral tertiary amine-catalyzed asymmetric γ-regioselective (4 + 3) annulation reaction of isatin-derived Morita-Baylis-Hillman carbonates and 1-azadienes was developed, delivering chiral azepane spirooxindoles with excellent stereoselectivity.
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Phosphine‐Catalyzed Activation of Alkylidenecyclopropanes: Rearrangement to Form Polysubstituted Furans and Dienones
TL;DR: A phosphine-catalyzed ring opening of electron-deficient alkylidenecyclopropylketones is reported to generate allylic phosphonium zwitterions that resemble the well-studiedosphine-allene adducts but exhibit distinct properties.
References
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Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions
Takuya Hashimoto,Keiji Maruoka +1 more
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The chemistry of recently isolated naturally occurring quinazolinone alkaloids
TL;DR: A concise account of the isolation, bioactivity, and synthesis of bioactive quinazolinone-based natural products for the period 1983-2005 is given in this paper.
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Phosphine catalysis of allenes with electrophiles
TL;DR: This tutorial review presents selected examples of nucleophilic phosphine catalysis using allenes and electrophiles for the generation of highly functionalized carbocycle or heterocycle structural motifs.
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Enantioselective Phosphine Organocatalysis
TL;DR: The broad potential synthetic usefulness of phosphine-promoted reactions has stimulated many recent investigations on enantioselective variants of known reactions of this family, as well as the search for new, specifically designed, chiral phosphorus catalysts as mentioned in this paper.
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Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs
Yi Chiao Fan,Ohyun Kwon +1 more
TL;DR: The reactivities of these phosphonium zwitterions, the applications of phosphine catalysis in the syntheses of biologically active compounds and natural products, and recent developments in the enantioselective phosphineCatalysis are described.