ArticleJournal of the American Chemical Society2014
An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst.
Article in Journal of the American Chemical Society, 2014. 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, 60 citations in OpenAlex.
- Bifunctional Monothiosquaramide-Catalyzed Enantioselective Addition of Masked Acyl Cyanide to Isatins: Umpolung Strategy for the Total Synthesis of (Organic letters · 2026Article
- Electrochemical synthesis of allenyl silanes and allenyl boronic esters.Nature communications · 2025Article
- Iron-Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- 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
- A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing aJournal of the American Chemical Society · 2020Article
- Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazinesRSC advances · 2019Article
- Article
- Delayed catalyst function enables direct enantioselective conversion of nitriles to NHScience (New York, N.Y.) · 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
- Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones.Angewandte Chemie (International ed. in English) · 2017Article
- Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.Journal of the American Chemical Society · 2017Article
- Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl-B(pin) Compounds to Ketones and α-Ketoesters.Angewandte Chemie (International ed. in English) · 2016Article
- Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.Nature chemistry · 2016Article
- Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.Angewandte Chemie (International ed. in English) · 2016Article
- Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update.Beilstein journal of organic chemistry · 2016Review
- N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.Tetrahedron letters · 2015Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A practical catalytic method for enantioselective addition of an allene unit to aldimines is disclosed. Transformations are promoted by an in-situ-generated B-based catalyst that is derived from a simple, robust, and readily accessible (in multigram quantities) chiral aminoalcohol. A range of aryl-, heteroaryl-, and alkyl-substituted homoallenylamides can be obtained in 66-91% yield and 84:16 to >99:1 enantiomeric ratio through reactions performed at ambient temperature and in the presence of 0.1-3.0 mol% of the chiral catalyst and a commercially available allenylboron reagent. The catalytic protocol does not require strict anhydrous conditions, can be performed on gram scale, and promotes highly selective addition of an allenyl unit (vs a propargyl group). The utility of the approach is demonstrated through development of succinct approaches to syntheses of anisomycin and epi-cytoxazone.
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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.