Journal ArticleDOI
Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach
TLDR
The key steps to the first asymmetric synthesis involved enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center.Abstract:
Optically pure hinckdentine A was synthesized on a 300 mg scale via an asymmetric catalysis-based strategy. The key steps to the first asymmetric synthesis involved (i) enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center, (ii) Beckmann fragmentation-mediated ring expansion, (iii) rearrangement-based introduction of an anilinic nitrogen atom, (iv) regioselective tribromination, and (v) final closure of the cyclic amidine moiety.read more
Citations
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Journal ArticleDOI
Catalytic asymmetric dearomatization (CADA) reaction-enabled total synthesis of indole-based natural products
Chao Zheng,Shu-Li You +1 more
TL;DR: This review presents the recent contributions inalytic asymmetric dearomatization reactions of indole derivatives and describes the synthetic details according to their different dearomative cyclization strategies.
Journal ArticleDOI
Recent progress in transition-metal-catalyzed enantioselective indole functionalizations.
Jing-Biao Chen,Yi-Xia Jia +1 more
TL;DR: This review summarizes the major achievements in the transition-metal-catalyzed enantioselective indole functionalization reactions since 2010 and focuses on C-C bond formation processes, including alkylations, arylations, cycloaddition reactions, and other reactions.
Journal ArticleDOI
Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence.
TL;DR: Palladium-catalyzed enantioselective dearomative arylalkynylation of N-substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL-based phosphoramidite as the chiral ligand.
Journal ArticleDOI
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines
TL;DR: A nickel-catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity.
Journal ArticleDOI
Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction.
TL;DR: Synthetic applications based on transformations of the exocyclic double bonds were realized without loss of enantiopurities, including hydrogenation, hydroborylation, and stereospecific ring-expanding rearrangement.
References
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Journal ArticleDOI
Escape from flatland: increasing saturation as an approach to improving clinical success.
TL;DR: It is demonstrated that saturation correlates with solubility, an experimental physical property important to success in the drug discovery setting, and both complexity and the presence of chiral centers correlate with success as compounds transition from discovery, through clinical testing, to drugs.
Journal ArticleDOI
Catalytic Asymmetric Dearomatization Reactions
TL;DR: The CADA reactions discussed herein include oxidative dearomatization reactions, dearomAtization by Diels-Alder and related reactions, the alkylative dearom atization of electron-rich arenes, transition-metal-catalyzed dearomatography reactions, cascade sequences involving asymmetric dearmatization as the key step, and nucleophilic dearomATization reactions of pyridinium derivatives.
Journal ArticleDOI
Dearomatization Strategies in the Synthesis of Complex Natural Products
Stéphane P. Roche,John A. Porco +1 more
TL;DR: This Review highlights recent developments concerning dearomatization, a powerful strategy for the total synthesis of architecturally complex natural products wherein planar, aromatic scaffolds are converted to three-dimensional molecular architectures.
Journal ArticleDOI
Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions
TL;DR: The combined results of this effort provide not only methods for the efficient synthesis of highly enantioenriched fused and spiro polycycles but also novel strategies in the field of asymmetric catalysis.