Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: scope and limitations |
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| Institution: | 1. Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, C/Marcel·lí Domingo, s/n. 43007 Tarragona, Spain;2. Istuto di Chimica Biomolecolare, CNR, tr. La Crucca 3, Li Punti, 070 Sassari, Italy;1. Dipartimento di Scienze, Università della Basilicata, Via dell''Ateneo Lucano, 85100 Potenza, Italy;2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Flemingovo námĕstí 2, 16610 Prague, Czech Republic;3. CNR, Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM-CNR), UOS di Pisa, Area della Ricerca, via G. Moruzzi 1, 56124 Pisa, Italy;4. Dipartimento di Medicina Molecolare e Traslazionale, Università di Brescia, Viale Europa 11, 25123 Brescia, Italy;1. KIT, Institute of Technical Thermodynamics and Refrigeration Engineering, Engler-Bunte-Ring 21, D-76131, Karlsruhe, Germany;2. University of Kaiserslautern, Laboratory of Engineering Thermodynamics, Erwin-Schrödinger-Straße 44, D-67663, Kaiserslautern, Germany;3. Martin-Luther University Halle-Wittenberg, Institute of Chemistry/Physical Chemistry, von-Danckelmann-Platz 3, D-06120, Halle, Germany;1. Department of Chemistry, Colorado State University, Fort Collins, CO 80523, United States;2. Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey;1. Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India;2. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India |
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| Abstract: | The ligand design of one of the most successful monophosphite ligand classes in Rh-catalyzed hydrogenation was expanded upon by introducing several substituents at the C-3 position of the furanoside backbone. A small but structurally important library of monophosphite ligands was developed by changing the substituents at the C-3 position of the furanoside backbone and the substituents/configurations at the biaryl phosphite group. These new furanoside monophosphite ligands were evaluated in the Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated carboxylic acid derivatives and enamides. The results show that the effect of introducing a substituent at the C-3 position of the furanoside backbone on the enantioselectivity depends not only on the configuration at the C-3 position of the furanoside backbone and the binaphthyl group but also on the substrate. Thus, the new ligands afforded high to excellent enantioselectivities in the reduction of carboxylic acid derivatives (ee’s up to >99.9%) and moderate ee’s (up to 67%) in the hydrogenation of enamides. |
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