ArticleJournal of the American Chemical Society2023
Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.
Article in Journal of the American Chemical Society, 2023. 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.
- Catalytic Enantioselective Intramolecular Aza-Michael Addition to α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2026Article
- Spiro-Linked Polyketides from Cultures ofJournal of natural products · 2026Article
- Catalytic Enantioselective Dearomatizing [2,3]-Wittig Rearrangements Allow Divergent [2,3]-, [1,2]-, and Sommelet-Hauser-Type Products.Journal of the American Chemical Society · 2026Article
- Enantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.Journal of the American Chemical Society · 2025Article
- Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective.The Journal of organic chemistry · 2024Article
- Asymmetric total syntheses of sarglamides A, C, D, E, and F.Chemical science · 2024Article
- Scaffold-Oriented Asymmetric Catalysis: Conformational Modulation of Transition State Multivalency during a Catalyst-Controlled Assembly of a Pharmaceutically Relevant Atropisomer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Multiple hydrogen-bonded dimers: are only the frontier atoms relevant?Physical chemistry chemical physics : PCCP · 2024Article
- Article
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Authors and funding
5 authors.
Funding
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Abstract
A bifunctional iminophosphorane (BIMP)-catalyzed, enantioselective intramolecular oxa-Michael reaction of alcohols to tethered, low electrophilicity Michael acceptors is described. Improved reactivity over previous reports (1 day vs 7 days), excellent yields (up to 99%), and enantiomeric ratios (up to 99.5:0.5 er) are demonstrated. The broad reaction scope, enabled by catalyst modularity and tunability, includes substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs), oxaspirocycles, sugar and natural product derivatives, dihydro-(iso)-benzofurans, and iso-chromans. A state-of-the-art computational study revealed that the enantioselectivity originates from the presence of several favorable intermolecular hydrogen bonds between the BIMP catalyst and the substrate that induce stabilizing electrostatic and orbital interactions. The newly developed catalytic enantioselective approach was carried out on multigram scale, and multiple Michael adducts were further derivatized to an array of useful building blocks, providing access to enantioenriched biologically active molecules and natural products.
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