ArticleAngewandte Chemie (International ed. in English)2024
Diastereoselective Hydrogenation of Tetrasubstituted Olefins using a Heterogeneous Pt-Ni Alloy Catalyst.
Article in Angewandte Chemie (International ed. in English), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 12 citations in OpenAlex.
- Highly selective and practical hydrogenation of functionalized (hetero)arenes.Nature communications · 2026Article
- Tailoring Pt-Cu Alloy Surfaces to Enhance OH Adsorption for Stereoselective Directed Hydrogenation.ACS catalysis · 2025Article
- A Catalytic Asymmetric Intramolecular [4 + 1]-Cycloaddition for the Total Synthesis of Terpene Alkaloid Natural Products.Journal of the American Chemical Society · 2025Article
- COAngewandte Chemie (International ed. in English) · 2025Article
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5 authors at 1 institution in 1 country.
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Abstract
Stereoselective hydrogenation of tetrasubstituted olefins is an attractive method to access compounds with two contiguous stereocenters. However, homogeneous catalysts for enantio- and diastereoselective hydrogenation exhibit low reactivity toward tetrasubstituted olefins due to steric crowding between the ligand scaffold and the substrate. Monometallic heterogeneous catalysts, on the other hand, provide accessible surface active sites for hindered olefins but exhibit unpredictable and inconsistent stereoinduction. In this work, we develop a Pt-Ni bimetallic alloy catalyst that can diastereoselectively hydrogenate unactivated, sterically-bulky tetrasubstituted olefins, utilizing the more oxophilic Ni atoms to adsorb a hydroxyl directing group and direct facially-selective hydrogen addition to the olefin via the Pt atoms. Structure-activity studies on several Pt-Ni compositions underscore the importance of exposing a uniform PtNi alloy surface to achieve high diastereoselectivity and minimize side reactions. The optimized Pt-Ni/SiO
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