ArticleACS catalysis2019
Site-selective acylation of natural products with BINOL-derived phosphoric acids.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 35 citations in OpenAlex.
- Development of CPA-Catalyzed β-Selective Reductive Amination of Cardenolides for the Synthesis and Biological Evaluation of Hydrolytically Stable Analogs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Applying statistical modeling strategies to sparse datasets in synthetic chemistry.Science advances · 2025Review
- Carbene-catalyzed chirality-controlled site-selective acylation of saccharides.Nature communications · 2025Article
- Advances, opportunities, and challenges in methods for interrogating the structure activity relationships of natural products.Natural product reports · 2024Review
- Utopia Point Bayesian Optimization Finds Condition-Dependent Selectivity forJournal of the American Chemical Society · 2024Article
- Article
- Asymmetric Photochemical [2 + 2]-Cycloaddition of Acyclic Vinylpyridines through Ternary Complex Formation and an Uncontrolled Sensitization Mechanism.Journal of the American Chemical Society · 2022Article
- Catalytic asymmetric and stereodivergent oligonucleotide synthesis.Science (New York, N.Y.) · 2021Article
- A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Experimental and Computational Studies on Regiodivergent Chiral Phosphoric Acid Catalyzed Cycloisomerization of Mupirocin Methyl Ester.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
5 authors at 3 institutions in 1 country.
Funding
Abstract
The site-selective acylation of a steroidal natural product 19-hydroxydehydroepiandrosterone catalyzed by 1,1'-Bi(2-napthol)-derived (BINOL) chiral phosphoric acids (CPA's) is described. Systematic variation and multivariate linear regression analysis reveal that the same steric parameters typically needed for high enantioselectivity with this class of CPAs are also required for site-selectivity in this case. Density functional theory calculations identify additional weak CH-π interactions as contributors to site discrimination. We further report a rare example of site-selective acylation of phenols through the evaluation of naringenin, a flavonoid natural product, using CPA catalysis. These results suggest that BINOL-derived CPA's may have broader applications in site-selective catalysis.
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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.