ArticleJournal of the American Chemical Society2015
Phosphine-Catalyzed Doubly Stereoconvergent γ-Additions of Racemic Heterocycles to Racemic Allenoates: The Catalytic Enantioselective Synthesis of Protected α,α-Disubstituted α-Amino Acid Derivatives.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Low-Molecular-Weight Organogelators Based onMaterials (Basel, Switzerland) · 2023Article
- Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings.Journal of the American Chemical Society · 2022Article
- Exploiting the Chiral Ligands ofMolecules (Basel, Switzerland) · 2021Article
- A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts.Organometallics · 2021Article
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 2020Article
- Design, synthesis and application of a new type of bifunctionalChemical science · 2019Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.Chemical science · 2017Article
- Caution in the Use of Nonlinear Effects as a Mechanistic Tool for Catalytic Enantioconvergent Reactions: Intrinsic Negative Nonlinear Effects in the Absence of Higher-Order Species.Journal of the American Chemical Society · 2017Article
- Catalytic Enantioselective Carbon-Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C-H Bonds.Journal of the American Chemical Society · 2016Article
- Asymmetric cyanation of imines via dipeptide-derived organophosphine dual-reagent catalysis.Nature communications · 2016Article
- Diastereoselective synthesis of vicinal tertiary andChemical science · 2016Article
- Enantioconvergent catalysis.Beilstein journal of organic chemistry · 2016Review
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2 authors.
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Abstract
Methods have recently been developed for the phosphine-catalyzed asymmetric γ-addition of nucleophiles to readily available allenoates and alkynoates to generate useful α,β-unsaturated carbonyl compounds that bear a stereogenic center in either the γ or the δ position (but not both) with high stereoselectivity. The utility of this approach would be enhanced considerably if the stereochemistry at both termini of the new bond could be controlled effectively. In this report, we describe the achievement of this objective, specifically, that a chiral phosphepine can catalyze the stereoconvergent γ-addition of a racemic nucleophile to a racemic electrophile; through the choice of an appropriate heterocycle as the nucleophilic partner, this new method enables the synthesis of protected α,α-disubstituted α-amino acid derivatives in good yield, diastereoselectivity, and enantioselectivity.
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