ArticleJournal of the American Chemical Society2017
Lithium Enolates in the Enantioselective Construction of Tetrasubstituted Carbon Centers with Chiral Lithium Amides as Noncovalent Stereodirecting Auxiliaries.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 75 citations in OpenAlex.
- Transient Boryl Assistance Enables Stereoselective Alkylation of Acyclic Tetrasubstituted Enolates.Angewandte Chemie (International ed. in English) · 2026Article
- The challenges of direct Claisen-Schmidt condensation in the synthesis of polyhydroxylated bischalcones: experimental results supported by DFT calculations.Beilstein journal of organic chemistry · 2026Article
- Photoenolization ofJournal of the American Chemical Society · 2025Article
- Copper(I)-Catalyzed Enantioselective α-Alkylation of 2-Acylimidazoles.Journal of the American Chemical Society · 2024Article
- A biocatalytic platform for asymmetric alkylation of α-keto acids by mining and engineering of methyltransferases.Nature communications · 2023Article
- Catalytic asymmetric defluorinative allylation of silyl enol ethers.Chemical science · 2023Article
- Asymmetric reactions involving aryne intermediates.Nature reviews. Chemistry · 2023Review
- Copper(I)-catalyzed asymmetric alkylation of α-imino-esters.Nature communications · 2023Article
- Diastereo- and Enantioselective Reductive Mannich-type Reaction of α,β-Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected βChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Lithium Enolate with a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine.Angewandte Chemie (International ed. in English) · 2022Article
- CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.Journal of the American Chemical Society · 2021Article
- Mechanism and Origins of Stereoselectivity of the Aldol-Tishchenko Reaction of Sulfinimines.The Journal of organic chemistry · 2021Article
- Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.Journal of the American Chemical Society · 2020Article
- Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation.Journal of the American Chemical Society · 2019Article
- Phosphonate-Directed Catalytic Asymmetric Hydroboration: Delivery of Boron to the More Substituted Carbon, Leading to Chiral Tertiary Benzylic Boronic Esters.ACS catalysis · 2018Article
- Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly.Journal of the American Chemical Society · 2017Article
- Direct Asymmetric Alkylation of Ketones: Still Unconquered.Angewandte Chemie (International ed. in English) · 2017Review
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
Abstract
Lithium enolates derived from carboxylic acids are ubiquitous intermediates in organic synthesis. Asymmetric transformations with these intermediates, a central goal of organic synthesis, are typically carried out with covalently attached chiral auxiliaries. An alternative approach is to utilize chiral reagents that form discrete, well-defined aggregates with lithium enolates, providing a chiral environment conducive of asymmetric bond formation. These reagents effectively act as noncovalent, or traceless, chiral auxiliaries. Lithium amides are an obvious choice for such reagents as they are known to form mixed aggregates with lithium enolates. We demonstrate here that mixed aggregates can effect highly enantioselective transformations of lithium enolates in several classes of reactions, most notably in transformations forming tetrasubstituted and quaternary carbon centers. Easy recovery of the chiral reagent by aqueous extraction is another practical advantage of this one-step protocol. Crystallographic, spectroscopic, and computational studies of the central reactive aggregate, which provide insight into the origins of selectivity, are also reported.
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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.