ArticleJournal of the American Chemical Society2016
Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Total synthesis of natural products based on hydrogenation of aromatic rings.Beilstein journal of organic chemistry · 2026Review
- Asymmetric arene hydrogenation: towards sustainability and application.Chemical Society reviews · 2023Review
- Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation.Chemical reviews · 2022Review
- Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.Chemical science · 2021Article
- Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.Journal of the American Chemical Society · 2021Article
- Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.Journal of the American Chemical Society · 2021Article
- Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.Angewandte Chemie (International ed. in English) · 2019Review
- A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes.Chemical science · 2019Article
- Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ACS catalysis · 2018Article
- Expanding the medicinal chemistry synthetic toolbox.Nature reviews. Drug discovery · 2018Review
- Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.Organic letters · 2018Article
- Metal-Free Cycloetherification by in Situ Generated P-Stereogenic α-Diazanium Intermediates: A Convergent Synthesis of Enantiomerically Pure Dihydrobenzooxaphospholes.Organic letters · 2017Article
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Authors and funding
29 authors.
Funding
Abstract
A concise asymmetric synthesis of an 11β-HSD-1 inhibitor has been achieved using inexpensive starting materials with excellent step-economy at low catalyst loadings. The catalytic enantioselective total synthesis of 1 was accomplished in 7 steps and 38% overall yield aided by the development of an innovative, sequential strategy involving Pd-catalyzed pyridinium C-H arylation and Ir-catalyzed asymmetric hydrogenation of the resulting fused tricyclic indenopyridinium salt highlighted by the use of a unique P,N-ligand (MeO-BoQPhos) with 1000 ppm of [Ir(COD)Cl]
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