ArticleNature communications2019
Catalytic enantioselective addition of organometallics to unprotected carboxylic acids.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 37 citations in OpenAlex.
- Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes.Organic letters · 2024Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents toOrganic letters · 2022Article
- Cu(I)-Catalyzed Alkynylation of Quinolones.Organic letters · 2022Article
- Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions.ACS catalysis · 2021Article
- Copper-Catalyzed Addition of Grignard Reagents to in situ Generated Indole-Derived Vinylogous Imines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Lewis Acid Promoted Dearomatization of Naphthols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Nucleophilic Dearomatization of N-Heteroaromatics Enabled by Lewis Acids and Copper Catalysis.Journal of the American Chemical Society · 2020Article
- CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.Organic letters · 2020Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Conjugate addition of organometallics to carbonyl based Michael acceptors is a widely used method that allows the building of new carbon-carbon (C-C) bonds and the introduction of chirality in a single step. However, conjugate additions to the simplest Michael acceptors, namely unprotected, unsaturated carboxylic acids, are considered to be prohibited by the fact that acid-base reactions overpower any other type of reactivity, including nucleophilic addition. Here we describe a transient protecting group strategy that allows efficient catalytic asymmetric additions of organomagnesium reagents to unprotected α,β-unsaturated carboxylic acids. This unorthodox pathway is achieved by preventing the formation of unreactive carboxylate salts by means of a reactive intermediate, allowing modifications of the carbon chain to proceed unhindered, while the stereochemistry is controlled with a chiral copper catalyst. A wide variety of β-chiral carboxylic acids, obtained with excellent enantioselectivities and yields, can be further transformed into valuable molecules through for instance catalytic decarboxylative cross-coupling reactions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.