Using the phospholane-phosphite ligand, BOBPHOS, almost perfect regioselectivities and high enantioselectivities (up to 92% ee) are observed in Rh catalysed enantioselective hydroformylation of vinyl arenes. This can be achieved under solvent-free conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c3cc48823c | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Supramolecular bidentate rhodium(I) or iridium(I) phosphine and oxazoline amino acid bioconjugates as selective catalysts for enantioselective reactions.
Dalton Trans
January 2025
Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia.
This publication describes monodentate phosphine and oxazoline ligands attached to an amino acid ester and the application of their supramolecularly assembled rhodium(I) or iridium(I) complexes in asymmetric catalysis. The major feature of these complexes is the transmission of chirality from distant hydrogen bonded amino acids to the prochiral catalytic metal center ("backdoor induction"). The generated homoleptic and heteroleptic rhodium(I) or iridium(I) precatalysts were studied by NMR, UV-VIS and CD spectroscopy as well as X-ray single crystal diffraction.
View Article and Find Full Text PDFRhodium-Catalyzed Asymmetric Reductive Hydroformylation of α-Substituted Enamides.
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.
Chiral γ-amino alcohols are prevalent structural motifs in natural products and bioactive compounds. Nevertheless, efficient and atom-economical synthetic methods toward enantiomerically enriched γ-amino alcohols are still lacking. In this study, a highly enantioselective rhodium-catalyzed reductive hydroformylation of readily available α-substituted enamides is developed, providing a series of pharmaceutically valuable chiral 1,3-amino alcohols in good yields and excellent enantioselectivities in a single step.
View Article and Find Full Text PDFStereoselective Synthesis of -2,4-Disubstituted Tetrahydrofurans via a Pd-Catalyzed Hayashi-Heck Arylation and Rh-Catalyzed Hydroformylation Sequence.
J Org Chem
August 2024
Department of Synthetic Molecule Process Chemistry, Genentech, Inc., South San Francisco, California 94080, United States.
A catalytic, two-step protocol for the expedient synthesis of -2,4-disubstituted tetrahydrofurans is described. In the first step, an enantioselective and regioselective Pd-catalyzed Hayashi-Heck arylation was developed using ()-hexaMeOBiphep to generate 5-aryl-2,3-dihydrofurans. A subsequent Rh-catalyzed hydroformylation step proceeds at low Rh loading with high regio- and diastereoselectivity for the -2,4-disubstituted tetrahydrofuran isomer.
View Article and Find Full Text PDFChemo-, regio- and enantioselective hydroformylation of trisubstituted cyclopropenes: access to chiral quaternary cyclopropanes.
Nat Commun
July 2024
Department of Chemistry and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, University of Science and Technology, Southern, 1088 Xueyuan Road, Shenzhen, 518055, China.
Catalytic asymmetric synthesis of polysubstituted chiral cyclopropane presents a significant challenge in organic synthesis due to the difficulty in enantioselective control. Here we report a rhodium-catalyzed highly chemo-, regio- and enantioselective hydroformylation of trisubstituted cyclopropenes affording chiral quaternary cyclopropanes. Importantly, the easy made sterically bulky ligand L1 can effectively suppress hydrogenation and decomposition reactions and give quaternary cyclopropanes with high regio- and enantioselectivities for both aryl and alkyl functionalized substrates.
View Article and Find Full Text PDFCuH-Catalyzed Regio- and Enantioselective Formal Hydroformylation of Vinyl Arenes.
J Am Chem Soc
May 2024
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
A highly enantioselective formal hydroformylation of vinyl arenes enabled by copper hydride (CuH) catalysis is reported. Key to the success of the method was the use of the mild Lewis acid zinc triflate to promote the formation of oxocarbenium electrophiles through the activation of diethoxymethyl acetate. Using the newly developed protocol, a broad range of vinyl arene substrates underwent efficient hydroacetalization reactions to provide access to highly enantioenriched α-aryl acetal products in good yields with exclusively branched regioselectivity.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!