Enantioselective hydrogenation of diaryl-substituted α,β-unsaturated nitriles |
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Authors: | Tobias C Wabnitz Carsten Götte Tiziana Benincori |
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Institution: | a Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany b Istituto di Scienze e Tecnologie Molecolari, Consiglio Nazionale delle Ricerche, via Golgi, 19, 20133-Milano, Italy c Institut für Pharmazie, Universität Regensburg, D-93040 Regensburg, Germany d Dipartimento di Scienze Chimiche ed Ambientali, Università dell’Insubria, via Valleggio 11, 22100-Como, Italy |
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Abstract: | α,β-Unsaturated nitriles can be hydrogenated with enantioselectivities up to 88% ee using chiral ruthenium-diphenylphosphino bisaryl and bisheteroaryl complexes such as ruthenium(II)-BINAP and ruthenium(II)-BINP. Mechanistic investigations indicate that conversion is accelerated by electron-rich ligands and that an additional coordinative group needs be present in order to promote conversion. The chiral products are useful building blocks for the synthesis of histamine H2 agonists of the arpromidine type. |
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