ArticleNature2013
Simple organic molecules as catalysts for enantioselective synthesis of amines and alcohols.
Article in Nature, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.
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Who cites it
43 citing papers in PubMed, 216 citations in OpenAlex.
- Predicting the stereoselectivity of chemical reactions by composite machine learning method.Scientific reports · 2024Article
- Asymmetric organocatalytic synthesis of chiral homoallylic amines.Beilstein journal of organic chemistry · 2024Review
- Beyond Stereoisomeric Effects: Exploring the Importance of Intermolecular Electron Spin Interactions in Biorecognition.The journal of physical chemistry letters · 2023Article
- Article
- Asymmetric Reactions ofMolecules (Basel, Switzerland) · 2023Review
- Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines.RSC advances · 2023Article
- New boro amino amide organocatalysts for asymmetric cross aldol reaction of ketones with carbonyl compounds.RSC advances · 2023Article
- Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.Nature communications · 2021Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- Access to 3,3-disubstituted oxindolesRSC advances · 2021Article
- Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.Angewandte Chemie (International ed. in English) · 2020Review
- Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NHAngewandte Chemie (International ed. in English) · 2020Article
- Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.Journal of the American Chemical Society · 2020Article
- A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing aJournal of the American Chemical Society · 2020Article
- Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.Angewandte Chemie (International ed. in English) · 2019Article
- A Regio- and Stereodivergent Synthesis of Homoallylic Amines by a One-Pot Cooperative-Catalysis-Based Allylic Alkylation/Hofmann Rearrangement Strategy.Angewandte Chemie (International ed. in English) · 2019Review
- Article
- Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides.Nature communications · 2019Article
- γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.Angewandte Chemie (International ed. in English) · 2018Article
- Catalytic, Enantioselective Synthesis of Allenyl Boronates.ACS catalysis · 2018Article
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7 authors at 1 institution in 1 country.
Funding
Abstract
The discovery of catalysts that can be used to synthesize complex organic compounds by enantioselective transformations is central to advances in the life sciences; for this reason, many chemists aim to discover catalysts that allow for preparation of chiral molecules as predominantly one mirror-image isomer. The ideal catalyst should not contain precious elements and should bring reactions to completion in a few hours through operationally simple procedures. Here we introduce a set of small organic molecules that can catalyse reactions of unsaturated organoboron reagents with imines and carbonyls; the products of the reactions are enantiomerically pure amines and alcohols, which might serve as intermediates in the preparation of biologically active molecules. A distinguishing feature of this catalyst class is the presence of a 'key' proton embedded within their structure. Catalysts are derived from the abundant amino acid valine and are prepared in large quantities in four steps with inexpensive reagents. Reactions are scalable, do not demand stringent conditions, and can be performed with as little as 0.25 mole per cent catalyst in less than six hours at room temperature to generate products in more than 85 per cent yield and ≥97:3 enantiomeric ratio. The efficiency, selectivity and operational simplicity of the transformations and the range of boron-based reagents are expected to render this advance important for future progress in syntheses of amines and alcohols, which are useful in chemistry, biology and medicine.
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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.