- Rooney T.P.C.
- Filippakopoulos P.
- Fedorov O.
- Picaud S.
- Cortopassi W.A.
- Hay D.A.
- Martin S.
- Tumber A.
- Rogers C.M.
- Philpott M.
- Wang M.
- Thompson A.L.
- Heightman T.D.
- Pryde D.C.
- Cook A.
- Paton R.S.
- Müller S.
- Knapp S.
- Brennan P.E.
- Conway S.J.
2. Chiral pool and auxiliary approaches: the first choice
3. Catalytic enantioselective reduction of quinoxalinones
3.1 Reduction mediated by organocatalytic systems
3.2 Reduction mediated by metal-based systems
4. Organocatalytic enantioselective synthesis of 3,4-dihydroquinoxalin-2-ones
4.1 Cycloaddition reactions
4.2 Epoxide ring-opening/cyclization in one-pot and stepwise sequence
4.3 Combined with photoredox catalysis
5. Conclusion and outlook
The bigger picture
- •Today, the continuous development of new catalytic and selective processes has become a pressing need to achieve sustainable chemical productions. Asymmetric catalysis is often required for the synthesis of drugs and biologically active compounds, which significantly populate the pharmaceutical and agrochemical markets. In this context, asymmetric catalysis demonstrated to be a powerful and effective tool to expand the classical stoichiometric chiral pool and auxiliary based approaches to medicinally and synthetically important 3,4-dihydroquinoxalin-2-ones.
- •Catalysis provided by metal/ligand complexes and small organic molecules followed complementary pathways to access the 3,4-dihydroquinoxalin-2-one scaffold. The construction of the prochiral quinoxalinone precursor, in the most recurrent chiral ligand-Ir, Pd, Ru-catalysed hydrogenation reaction, is required. Conversely, the organocatalytic protocols, occasionally performable under more appealing one-pot conditions, involve cycloaddition or ring-opening/cyclization of readily available reagents and intermediates.
- •However, there is the need for further improvements in terms of more sustainable reaction conditions, substrate scope and most of all the development of enantioselective catalytic methods to hitherto hardly accessible 3,4-dihydroquinoxalin-2-ones, featuring quaternary stereocenters.
Declaration of competing interest
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