Journal ArticleDOI
Catalytic Asymmetric [4 + 1] Cyclization of Benzofuran-Derived Azadienes with 3-Chlorooxindoles.
TLDR
This reaction represents the first catalytic asymmetric cyclization of benzofuran-derived azadienes, and provides a useful strategy for the enantioselective construction of five-membered ring-based chiral spirooxindole scaffolds.Abstract:
A chiral guanidine-catalyzed asymmetric [4 + 1] cyclization of benzofuran-derived azadienes with 3-chlorooxindoles has been established, which constructed chiral spirooxindole frameworks with in situ generation of a five-membered ring with high diastereoselectivities (up to >95:5 dr) and good enantioselectivities (up to 94:6 er). This reaction represents the first catalytic asymmetric [4 + 1] cyclization of benzofuran-derived azadienes, which will enrich the research field of catalytic asymmetric cyclizations of such reactants. In addition, this reaction provides a useful strategy for the enantioselective construction of five-membered ring-based chiral spirooxindole scaffolds.read more
Citations
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Palladium-Catalyzed Asymmetric [4+3] Cyclization of Trimethylenemethane: Regio-, Diastereo-, and Enantioselective Construction of Benzofuro[3,2-b]azepine Skeletons
TL;DR: This reaction represents the first catalytic asymmetric [4 + 3] cyclization of Pd-trimethylenemethane (Pd-TMM), which would enrich arsenal of PD-T MM chemistry in organic synthesis.
Journal ArticleDOI
Recent Advances in the Construction of Trifluoromethyl‐Containing Spirooxindoles through Cycloaddition Reactions
TL;DR: In this minireview, recent advances in the construction of trifluoromethyl-containing spirooxindoles have been summerized and discussed, and the representative synthetic methodologies and the corresponding reaction mechanisms have been described.
Journal ArticleDOI
Construction of All-Carbon Quaternary Stereocenters via Sequential Photoactivation/Isothiourea Catalysis.
TL;DR: Highly enantioselective [4 + 2] cyclizations of azadienes with in situ generated ketenes were developed through sequential visible-light photoactivation/isothiourea catalysis, which offers a novel approach for the creation of all-carbon quaternary stereocenters through disubstituted C1-ammonium enolates.
Journal ArticleDOI
Palladium-Catalyzed Asymmetric [4+3]-Cyclization Reaction of Fused 1-Azadienes with Amino-trimethylenemethanes: Highly Stereoselective Construction of Chiral Fused Azepines
Prathibha Kumari,Weiwei Liu,Cheng-Jie Wang,Jun Dai,Mei-Xin Wang,Qi-Qiong Yang,Yu-Hua Deng,Zhihui Shao +7 more
Journal ArticleDOI
Enantioselective Synthesis of Benzofuran-Fused N-Heterocycles via Chiral Squaramide Catalyzed [4 + 2] Cyclization of Azadienes with Azlactones.
TL;DR: An asymmetric cyclization reaction of azadienes and azlactones was investigated by employing a Cinchona squaramide catalyst, which could afford a series of benzofuran-fused six-membered heterocycles containing a α,α-disubstituted amino acid unit in a highly diastereoselectives and enantioselective manner with good to excellent yields.
References
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Journal ArticleDOI
Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies
TL;DR: This review focuses on the enantioselective synthesis of spirooxindoles via organocascade strategies and is organized on the basis of three primary starting materials and then further subdivided according to the types of organocatalyst.
Journal ArticleDOI
Spirooxindoles: Promising scaffolds for anticancer agents.
Bin Yu,De-Quan Yu,Hong-Min Liu +2 more
TL;DR: This review highlights recent progress of biologically active spirooxindoles for their anticancer potentials, mainly focusing on the discussions of SARs and modes of action.
Journal ArticleDOI
Catalytic asymmetric synthesis of spirooxindoles: recent developments
Guang-Jian Mei,Feng Shi +1 more
TL;DR: This feature article outlines the recent progress in the catalytic asymmetric synthesis of spirooxindoles, including the contributions of the group of scientists from the University of California, Berkeley.
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Catalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels–Alder Reaction of In Situ Generated ortho‐Quinone Methides with 3‐Methyl‐2‐Vinylindoles
TL;DR: By selecting 3-methyl-2-vinylindoles as a class of competent dienophiles, this approach provides an efficient strategy to construct an enantioenriched chroman framework with three adjacent stereogenic centers in high yields and excellent stereoselectivities.
Journal ArticleDOI
Asymmetric catalytic cascade reactions for constructing diverse scaffolds and complex molecules.
Yao Wang,Hong Lu,Peng-Fei Xu +2 more
TL;DR: The development of the strategy of asymmetric organocatalytic relay cascades has provided a useful tool for the controlled synthesis of specific diastereomers in complex molecules and some of these reactions are highly efficient since catalyst loadings as low as 1 mol % can promote the multistep sequences affording complex architectures with high stereoselectivities and yields.