ArticleJournal of the American Chemical Society2010
Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Catalytic Transformations of Aza-Cyclobutenes, Fused Cyclobutenes, and Cyclobutenones.Chemical record (New York, N.Y.) · 2026Review
- Rhodium-Catalyzed Asymmetric Reductive Hydroformylation of α-Substituted Enamides.Journal of the American Chemical Society · 2024Article
- Substrate scope driven optimization of an encapsulated hydroformylation catalyst.Catalysis science & technology · 2024Article
- Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles.Angewandte Chemie (International ed. in English) · 2022Article
- Construction of a quaternary stereogenic center by asymmetric hydroformylation: a straightforward method to prepare chiral α-quaternary amino acids.Chemical science · 2022Article
- α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.The Journal of organic chemistry · 2018Article
- Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation.Nature communications · 2018Article
- KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation.Organic letters · 2016Article
- Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.Angewandte Chemie (International ed. in English) · 2016Review
- Rapid Asymmetric Transfer Hydroformylation (ATHF) of Disubstituted Alkenes Using Paraformaldehyde as a Syngas Surrogate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand.Organic letters · 2015Article
- Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.Angewandte Chemie (International ed. in English) · 2014Article
- Distal-selective hydroformylation using scaffolding catalysis.Journal of the American Chemical Society · 2014Article
- Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.Organic letters · 2014Article
- Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.Organic letters · 2014Article
- A highly step-economical synthesis of dictyostatin.Angewandte Chemie (International ed. in English) · 2013Article
- Enantioselective hydroformylation of aniline derivatives.The Journal of organic chemistry · 2011Article
- Regioselective hydroformylation of allylic alcohols.Organic letters · 2011Article
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5 authors.
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Abstract
Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral aldehydes with useful regioselectivity and high enantioselectivity (up to 99% ee). Chiral Roche aldehyde is obtained with 97% ee from the hydroformylation of allyl silyl ethers. Commonly difficult substrates such as 1,1- and 1,2-disubstituted alkenes undergo effective hydroformylation with 89-97% ee and complete conversion for six examples. Palladium-catalyzed aerobic oxidative amination of allyl benzyl ether followed by enantioselective hydroformylation yields the β(3)-aminoaldehyde with 74% ee.
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