Synthesis of enantiomerically pure (5S)-4-aza-2-oxa-6,6-dimethyl-7,10-methylene-5-spiro[4.5]decan-3-one, a novel chiral oxazolidin-2-one from (-)-camphene for use as a recyclable chiral auxiliary in asymmetric transformations

By an intramolecular nitreno-mediated route (-)-camphene is transformed into a novel spiro-oxazolidin-2-one whose efficiency as a chiral auxiliary is highlighted by the excellent levels of chiral induction attained in an array of asymmetric transformations such as the Diels-Alder, conjugate addition, aldol condensation, alkylation and acylation reactions