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DOI: 10.1055/s-0036-1589401
Asymmetric Hydrogenation of Cyclic Imines and Enamines: Access to 1,5-Benzodiazepine Pharmacophores
Publikationsverlauf
Received: 18. September 2016
Accepted: 30. September 2016
Publikationsdatum:
13. Oktober 2016 (online)
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Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday
Abstract
A new strategy towards the pharmacologically relevant class of dihydro-1,5-benzodiazepines was developed by applying a rhodium-catalyzed asymmetric hydrogenation. The approach represents an efficient protocol providing access to the optically active products in excellent yields (up to 99%) and with high enantioselectivities (up to 92% ee). The versatility of the methodology was demonstrated by a broad substrate scope including alkyl, aryl, and heteroaryl substituents as well as halides. Furthermore, investigations regarding the reaction mechanism were performed and unraveled a preferred reaction of the tautomeric enamine in the rhodium-catalyzed asymmetric hydrogenation.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589401.
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