ArticleAngewandte Chemie (International ed. in English)2019
Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
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Who cites it
8 citing papers in PubMed.
- Carbon and Heteroatom Activation via N-Heterocyclic Carbene-Bound Dearomative Intermediates for Stereoselective Annulation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Transition-metal-free approach to quinolinesFrontiers in chemistry · 2022Article
- NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions.Chemical science · 2021Review
- CFBeilstein journal of organic chemistry · 2021Review
- N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation.Communications chemistry · 2020Article
- A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.Angewandte Chemie (International ed. in English) · 2020Article
- An Update of Transition Metal-Catalyzed Decarboxylative Transformations of Cyclic Carbonates and Carbamates.Molecules (Basel, Switzerland) · 2019Review
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
A direct decarboxylative strategy for the generation of aza-o-quinone methides (aza-o-QMs) by N-heterocyclic carbene (NHC) catalysis has been discovered and explored. This process requires no stoichiometric additives in contrast with current approaches. Aza-o-QMs react with trifluoromethyl ketones through a formal [4+2] manifold to access highly enantioenriched dihydrobenzoxazin-4-one products, which can be converted to dihydroquinolones through an interesting stereoretentive aza-Petasis-Ferrier rearrangement sequence. Complementary dispersion-corrected density functional theory (DFT) studies provided an accurate prediction of the reaction enantioselectivity and lend further insight to the origins of stereocontrol. Additionally, a computed potential energy surface around the major transition structure suggests a concerted asynchronous mechanism for the formal annulation.
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Registered trials
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