Nonracemic Betti Base as a New Chiral Auxiliary:  Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins

Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)-isosolenopsins (as hydrochlorides) were achieved in four steps and in 80−82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH₂Cl₂.