(5AR,10BS)-(+)-5A,10B-DIHYDRO-2-(PENTAFLUOROPHENYL)-4H,6H-INDENO[2,1-B][1,2,4]TRIZOLO[4,3-D][1,4]OXAZINIUM TETRAFLUOROBORATE

Reaction

1. Reagent used in the highly enantioand diastereoselective, catalytic intramolecular Stetter reaction.
2. Direct synthesis of α-protio and α-deuterio α-chloro and α-fluoro carboxylic acids via asymmetric hydration.
3. Chemoselective conversion of α-unbranched aldehydes to amides.

Uses

5a(R),10b(S)-5a,10b-Dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate can be used as an N-heterocyclic carbene (NHC) organocatalyst in:

• Benzoin reactions of aldehydes and total synthesis of a natural product named isodarparvinol B.
• Synthesis of spirocyclic oxindole-dihydropyranones by reacting α-bromo-α,β-unsaturated aldehydes with isatin derivatives.
• Synthesis of 1,4-dicarbonyl compounds through intramolecular Stetter reaction.