Journal ArticleDOI
Phosphine-catalyzed [4 + 2] annulation of γ-substituent allenoates: facile access to functionalized spirocyclic skeletons.
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TLDR
The first phosphine-catalyzed [4 + 2] annulation of γ-substituted allenoates with 2-arylidene-1H-indenes-1,3(2H)-diones is disclosed, offering a powerful approach to the construction of highly substituted spiro[4.5]dec-6-ene skeletons in excellent yields, and with complete regioselectivity and high diastereoselectivities.About:
This article is published in Organic Letters.The article was published on 2013-06-06. It has received 113 citations till now. The article focuses on the topics: Annulation & Regioselectivity.read more
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[4+2] and [4+3] catalytic cycloadditions of allenes.
TL;DR: This feature review describes the development of catalytic [4+2] and [4-3] cycloadditions of allenes, as efficient and practical methodologies for assembling six and seven-membered cyclic systems.
Journal ArticleDOI
1,3-Dipolar cycloadditions of azomethine imines
TL;DR: Enantiocatalyzed 1,3-dipolar cycloadditions have been extensively considered and applied to the synthesis of a great variety of dinitrogenated heterocycles with biological activity and are present in many pharmaceuticals, agrochemicals and other useful chemicals.
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Highly enantioselective synthesis of 3,4-dihydropyrans through a phosphine-catalyzed [4+2] annulation of allenones and β,γ-unsaturated α-keto esters.
Weijun Yao,Xiaowei Dou,Yixin Lu +2 more
TL;DR: The synthetic value of the dihydropyran motif was demonstrated by a concise preparation of an anti-hypercholesterolemic agent by employing allene ketones as C2 synthons and β,γ-unsaturated α-keto esters as C4 synthons.
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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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Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine
TL;DR: The domino reactions presented in this report are valuable for highly stereoselective construction of complex structures under mild reaction conditions and have also been achieved with up to 93% ee.
References
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Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.
TL;DR: The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties.
Journal ArticleDOI
Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids
TL;DR: The spiro[pyrrolidine-3,3′-oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis as discussed by the authors.
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Lewis Base Catalysis in Organic Synthesis
TL;DR: It has become increasingly apparent that the behavior of Lewis bases as agents for promoting chemical reactions is not merely as an electronic complement of the cognate Lewis acids: in fact Lewis bases are capable of enhancing both the electrophilic and nucleophilic character of molecules to which they are bound.
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Reactions of electron-deficient alkynes and allenes under phosphine catalysis.
TL;DR: This study illuminates the unusual phenomena and shows how understanding of the central problem to generate a 1,3-dipole from alkynoates or allenoates by interaction with various phosphines allows control of the reaction.
Journal ArticleDOI
Nucleophilic Phosphine Organocatalysis
Joey L. Methot,William R. Roush +1 more
TL;DR: In this article, a mini-review presents recent advances in nucleophilic phosphine organocatalysis for carbon-carbon bond formation, showing that the accessibility of chiral phosphines has rendered several of these transformations enantioselective and has made possible the kinetic resolution of racemic secondary alcohols by phosphine-catalyzed acylation.
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Reactions of electron-deficient alkynes and allenes under phosphine catalysis.
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