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Journal ArticleDOI

Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position

Feng Zhou, +2 more
- 01 Jun 2010 - 
- Vol. 352, Iss: 9, pp 1381-1407
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TLDR
The catalytic asymmetric synthesis of the tetrasubstituted carbon stereocenter at the C-3 position of the oxindole framework integrates new synthetic methods and chiral catalysts.
Abstract
The 3,3′-disubstituted oxindole structural motif is a prominent feature in many alkaloid natural products, which include all kinds of tetrasubstituted carbon stereocenters, spirocyclic or not, all-carbon or heteroatom-containing. The catalytic asymmetric synthesis of the tetrasubstituted carbon stereocenter at the C-3 position of the oxindole framework integrates new synthetic methods and chiral catalysts, reflects the latest achievements in asymmetric catalysis, and facilitates the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. This review summarizes the recent progress in this area, and applications in the total synthesis of related bioactive compounds.

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Citations
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Journal ArticleDOI

Strategies for the enantioselective synthesis of spirooxindoles.

TL;DR: This review features efficient strategies for the enantioselective synthesis of spirocyclic oxindoles, focusing on reports in 2010 and 2011, and is organized based on two primary disconnection strategies, and then further subdivided into the type and ring size of the spirocycle that is generated.
Journal ArticleDOI

Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones

TL;DR: This review aims to cover the literature on asymmetric quaternary carbons, 2-substituted and 2,2'-disubtituted 3-indolinones, from its origin to the end of 2011.
Journal ArticleDOI

Catalytic Enantioselective Construction of Quaternary Stereocenters: Assembly of Key Building Blocks for the Synthesis of Biologically Active Molecules

TL;DR: This Account discovered that in the presence of catalytic palladium-pyridinooxazoline complex, arylboronic acids add smoothly to β-substituted cyclic enones to furnish ketones with a β-benzylic quaternary stereocenter in high yields and enantioselectivities.
Journal ArticleDOI

Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters.

TL;DR: The advances in the construction of all-carbon quaternary stereocenters via catalytic enantioselective desymmetrization of prochiral and meso-compounds are summarized and synthetic opportunities still available are outlined.
References
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Journal ArticleDOI

In the Golden Age of Organocatalysis

TL;DR: The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
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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

Asymmetric organocatalytic domino reactions.

TL;DR: This Minireview discusses the current development of domino reactions mediated by organocatalysts, as this principle is used very efficiently in the biosynthesis of complex natural products starting from simple precursors.
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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