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

Abstract

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