ArticleChemical science2020
Mechanism and origins of selectivity in the enantioselective oxa-Pictet-Spengler reaction: a cooperative catalytic complex from a hydrogen bond donor and chiral phosphoric acid.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Catalytic Enantioselective Synthesis of 1,1-Disubstituted Isochromans.Journal of the American Chemical Society · 2026Article
- Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet-Spengler Reaction and the Development of a Stereodivergent Variant.ACS catalysis · 2023Article
- The Characterization of a Novel D-allulose 3-Epimerase fromFoods (Basel, Switzerland) · 2022Article
- Identifying the true origins of selectivity in chiral phosphoric acid catalyzedChemical science · 2021Article
- Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.Journal of the American Chemical Society · 2021Article
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Authors and funding
7 authors.
Funding
Abstract
Enantioselective additions to oxocarbenium ions are high-value synthetic transformations but have proven challenging to achieve. In particular, the oxa-Pictet-Spengler reaction has only recently been rendered enantioselective. We report experimental and computational studies on the mechanism of this unusual transformation. Herein we reveal that this reaction is hypothesized to proceed through a self-assembled ternary hydrogen bonding complex involving the substrate, chiral phosphate ion, and a urea hydrogen-bond donor. The computed transition state reveals C2-symmetric grooves in the chiral phosphate that are occupied by the urea and substrate. Occupation of one of these grooves by the urea co-catalyst tunes the available reactive volume and enhances the stereoselectivity of the chiral phosphate catalyst.
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