Asymmetric Hydrogenation of Cyclic Imines and Enamines: Access to 1,5-Benzodiazepine Pharmacophores

Ruediger Borrmann, Rene M. Koenigs, Jochen Zoller, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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.

Original languageEnglish (US)
Article numberss-2016-z0648-op
Pages (from-to)310-318
Number of pages9
JournalSynthesis (Germany)
Volume49
Issue number2
DOIs
StatePublished - Jan 18 2017

Keywords

  • asymmetric hydrogenation
  • benzodiazepines
  • enamine
  • reduction
  • rhodium catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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