Journal ArticleDOI
Catalytic enantioselective stereoablative alkylation of 3-halooxindoles: facile access to oxindoles with C3 all-carbon quaternary stereocenters.
Sandy Ma,Xiaoqing Han,Xiaoqing Han,Shyam Krishnan,Shyam Krishnan,Scott C. Virgil,Scott C. Virgil,Brian M. Stoltz,Brian M. Stoltz +8 more
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TLDR
From 2 to 1!Abstract:
From 2 to 1! Racemic tertiary halooxindoles proceed to enantioenriched oxindoles bearing all-carbon quaternary stereocenters as a result of a catalytic enantioselective stereoablative process (see scheme). The application of this procedure allows for the rapid asymmetric construction of biologically significant alkaloid core motifs.read more
Citations
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Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position
Feng Zhou,Yun-Lin Liu,Jian Zhou +2 more
TL;DR: 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.
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
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
Total Synthesis of Indoline Alkaloids: A Cyclopropanation Strategy
Dan Zhang,Hao Song,Yong Qin +2 more
TL;DR: This Account summarizes efforts to develop a cascade or stepwise reaction of cyclopropanation/ring-opening/iminium cyclization (the CRI reaction) on tryptamine derivatives for assembling indoline alkaloid skeletons and highlights advances in construction of the three types of skeletons.
Journal ArticleDOI
Catalytic enantioconvergent coupling of secondary and tertiary electrophiles with olefins
TL;DR: Nickel-catalysed coupling of racemic alkyl electrophiles and olefins in the presence of a hydrosilane is achieved with good enantioselectivity and yield under very mild reaction conditions, which opens the door to developing more general methods for enantioconvergentAlkyl–alkyl coupling.
References
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Journal ArticleDOI
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.
Journal ArticleDOI
The asymmetric intramolecular Heck reaction in natural product total synthesis.
Amy B. Dounay,Larry E. Overman +1 more
Journal ArticleDOI
Chiral bis(oxazoline) copper(II) complexes: versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions.
TL;DR: X-ray crystallography of the chiral complexes reveals a propensity for the formation of distorted square planar or square pyramidal geometries in catalyzed processes that exhibit excellent temperature-selectivity profiles.
Journal ArticleDOI
Catalytic enantioselective construction of all-carbon quaternary stereocenters
Barry M. Trost,Chunhui Jiang +1 more
TL;DR: In this paper, a comprehensive account of the currently available methods of the above transformation that afford high enantioselectivities and synthetically useful yields is given. But this review is limited to all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents.
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Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position
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