We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Aminodecalone Scaffolds – Enantioselective Synthesis, Indole and Quinoline Annulation.
- Authors
Schäfer, Benjamin; Schmidtmann, Marc; Christoffers, Jens
- Abstract
Optically active benzo[b]carbazole and benzo[b]acridine derivatives were prepared by Fischer indole or Friedländer quinoline annulation from 2‐oxodecalone‐4a‐carboxylates with a quaternary stereocenter. As an additional point for diversification, the target compounds carry a nitro function, which was transformed to an amide or lactam after reduction. The scaffold itself was accessed by asymmetric, copper catalyzed Michael reaction of a β‐oxoester with methyl vinyl ketone utilizing l‐valine diethyl amide as chiral auxiliary. Two enantiopure, epimeric compounds were obtained with 99 % ee and 92 % ee, which were separated and in parallel sequences submitted to intramolecular aldol reaction and catalytic hydrogenation furnishing the 2‐oxodecalone scaffolds. As a precursor for the primary amino group, the scaffolds contained a nitro function at their 6‐positions, which was reduced at the end of the synthetic sequence. The relative and absolute configurations of all three stereocenters were established by X‐ray crystallography.
- Subjects
QUINOLINE; ANNULATION; CARBOXYLATES; X-ray crystallography; HYDROGENATION; ENANTIOSELECTIVE catalysis; CARBAZOLE derivatives
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 32, p4490
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201800931